Herbicidal sulfonamides

ABSTRACT

The invention relates to certain sulfonylurea compounds having an ester group ortho to the sulfonylurea linkage which have been found to be excellent preemergent and postemergent herbicides or plant growth regulators.

RELATED APPLICATION

This application is a continuation-in-part of my copending application U.S. Ser. No. 617,606 filed June 5, 1984 which is now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to certain novel sulfonylurea compounds, agriculturally suited compositions thereof and their use as preemergent and postemergent herbicides or plant growth regulants.

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

A number of different types of N-[(heterocyclic)aminocarbonyl]arylsulfonamides are known as herbicides.

U.S. Pat. No. 4,394,506 discloses sulfonylurea herbicides substituted on the benzene ring ortho to the sulfonylurea bridge.

U.S. Pat. No. 4,127,405 discloses sulfonylurea herbicides substituted ortho to the sulfonylurea segment.

U.S. Pat. No. 4,420,325 discloses sulfonylurea herbicides wherein the benzene ring is substituted ortho to the sulfonylurea substituent.

U.S. Pat. No. 4,383,113 discloses herbicidal ortho-carboalkoxybenzenesulfonylureas.

EP-A No. 30,142 published June 10, 1981 discloses herbicidal thiophene sulfonylureas substituted with alkoxycarbonyl groups.

EP-A No. 70,698 published Jan. 26, 1983 discloses herbicidal indole sulfonylureas.

Herbicidal pyrazole sulfonylureas are disclosed in EP-A-No. 95,925 published Dec. 7, 1983 and EP-A-No. 87,780 published Sept. 7, 1983.

The current population explosion and concomitant world food and fiber shortage demand improvement in the efficiency of producing these crops. Preventing or minimizing loss of valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency. Even though there are a wide variety of products useful for killing and inhibiting growth of undesired vegetation the need still exists for more effective herbicides.

SUMMARY OF THE INVENTION

Now new compounds and compositions thereof have been found that are preemergent or postemergent herbicides or plant growth regulants. The compounds of the invention are of the formula I ##STR1## wherein J is ##STR2## W is O or S; R is H or CH₃ ;

R₁ is C₂ -C₅ alkyl, C₄ alkenyl or C₄ alkynyl substituted with one or two substituents selected from: ##STR3## provided that (1) when R₁ is disubstituted, then the two substituents are identical and are not on the same carbon atom;

(2) when R₁ is C₂ -C₃ alkyl and monosubstituted, then the substituent is other than --SR₇ or --SO₂ R₇ ; and

(3) the carbon atom of R₁ adjacent to the ester oxygen does not carry any of the above substituents and must be substituted by at least one hydrogen atom;

W₁ is O or S;

n is 0, 1, or 2;

R₂ is H, Cl, F, Br, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkoxy, C₁ -C₃ haloalkylthio, C₁ -C₂ haloalkyl, or C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ ;

R₃ is H, F, Cl, CH₃ or OCH₃ ;

R₄ is H or CH₃ ;

R₅ is H, C₁ -C₃ alkyl, CH₂ CH═CH₂ or phenyl;

R₆ is H or C₁ -C₃ alkyl;

R₇ is C₁ -C₄ alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 methoxy groups or 0-1 cyano groups, C₃ -C₄ alkenyl substituted with 0-3 atoms of F, Cl or Br, C₃ -C₄ alkynyl or ##STR4## R₈ is H or C₁ -C₂ alkyl; R₉ is C₁ -C₂ alkyl;

R₁₀ is C₁ -C₄ alkyl or C₆ H₅ ;

R₁₁ and R₁₂ are independently H, F, Cl, Br, CH₃, OCH₃, SCH₃, SO₂ CH₃, NO₂ or CF₃ ;

A is ##STR5## X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, OCF₂ H, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃ or CF₃ ;

Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, NH₂, N(CH₃)₂, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, ##STR6## OCF₂ H, SCF₂ H, CH₂ S(O)_(p) (C₁ -C₄ alkyl), cyclopropyl or CH₂ OC₂ H₅ ;

m is 2 or 3;

p is 0, 1 or 2;

Q₁ and Q₂ are independently O or S;

R₁₃ is H or CH₃ ;

R₁₄ and R₁₅ are independently C₁ -C₂ alkyl;

R₁₆ is H, F, Cl or CH₃ ;

R₁₇ is C₁ -C₁₀ alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 methoxy groups or 0-1 cyano groups, C₃ -C₁₀ alkenyl substituted with 0-3 atoms of F, Cl or Br, C₃ -C₁₀ alkynyl substituted with 0-3 atoms of F, Cl or Br, or ##STR7## Z is CH or N; Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H;

X₂ is CH₃, C₂ H₅ or CH₂ CF₃ ;

Y₂ is OCH₃, OC₂ H₅, SCH₃, SC₂ H₅, CH₃ or CH₂ CH₃ ;

Y₃ is H or CH₃ ;

X₃ is CH₃ or OCH₃ ;

X₄ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl; and

Y₄ is CH₃, OCH₃, OC₂ H₅ or Cl;

provided that

(a) when W is S, then R is H,

A is ##STR8## and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CF₃, OCH₂ CH₂ OCH₃, CH(OCH₃)₂ or ##STR9## (b) when X is Cl, F or Br, then Z is CH and Y is OCH₃, OC₂ H₅, NH₂, N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂ H; and

(c) when X or Y is OCF₂ H, then Z is CH;

and their agriculturally suitable salts.

Compounds of the invention which are preferred for their higher herbicidal activity, greater plant growth regulant activity and/or more favorable ease of synthesis are:

(1) Compounds of Formula I wherein W is O; R is H; R₁ is monosubstituted C₂ -C₅ alkyl; R₇ is CH₃, C₂ H₅, C₃ alkenyl or C₃ alkynyl; R₉ is CH₃ ; R₁₀ is CH₃ ; and R₁₇ is C₁ -C₄ alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 methoxy groups or 0-1 cyano group, C₃ -C₄ alkenyl substituted with 0-3 atoms of F, Cl or Br or C₃ -C₄ alkynyl.

(2) Compounds of Preferred 1 wherein A is A-1; R₂ is H, F, Cl, CH₃, OCH₃, OC₂ H₅, SCH₃, SC₂ H₅, CH₂ OCH₃ or CF₃ ; R₆ is H; R₁₆ is H; and Y is CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, CH₂ OC₂ H₅, NHCH₃, N(CH₃)₂, cyclopropyl, CH(OCH₃)₂ or ##STR10## (3) Compounds of Preferred 2 wherein R₁₇ is CH₃, C₂ H₅ or CH₂ CH═CH₂ ; W₁ is O; and R₁ is monosubstituted C₂ -C₃ alkyl.

(4) Compounds of Preferred 3 wherein J is J-1 and R₂ is H.

(5) Compounds of Preferred 3 wherein J is J-2.

(6) Compounds of Preferred 3 wherein J is J-3.

(7) Compounds of Preferred 3 wherein J is J-4.

(8) Compounds of Preferred 3 wherein J is J-5.

(9) Compounds of Preferred 3 wherein J is J-6.

(10) Compounds of Preferred 3 wherein J is J-7.

(11) Compounds of Preferred 3 wherein J is J-8.

(12) Compounds of Preferred 3 wherein X is CH₃, OCH₃, OC₂ H₅, Cl, Br, OCHF₂ or CF₃ ; and Y is CH₃, OCH₃, NHCH₃ or CH(OCH₃)₂.

The compound of the invention which is specifically preferred for reasons of its highest herbicidal activity, greatest plant growth regulant activity and/or most favorable ease of synthesis is: 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester, m.p. 110°-113° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

Compounds of Formula I can be prepared by one or more of the procedures shown in Equations 1, 5, and 6. J, W, R, and A are as previously defined. ##STR11##

The reaction of Equation 1 is best carried out in an inert aprotic organic solvent such as dichloromethane, 1,2-dichloroethane, tetrahydrofuran, or acetonitrile, at a temperature between 20° and 85° C. The order of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate (or isothiocyanate), or a solution of it in the reaction solvent, to a stirred suspension of the amine.

In some cases, the desired product is insoluble in the reaction solvent at ambient temperature and crystallizes from it in pure form. Products soluble in the reaction solvent are isolated by evaporation of the solvent. Compounds of Formula I then may be purified by trituration of the evaporation residue with solvents such as 1-chlorobutane or ethyl ether and filtation, by recrystallization from mixtures of solvents such as 1,2-dichloroethane, 1-chlorobutane and heptane or by chromatography on silica gel.

Sulfonylisocyanates (II, W is O) are known in the art and are prepared from the corresponding sulfonamides (IV) by one of the following two general methods. ##STR12##

The sulfonamide IV and an alkyl isocyanate (e.g., n-butyl isocyanate) in xylene or other solvent boiling above 135° C. are mixed in the presence or absence of a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane (DABCO) and heated to 135°-140° C. After 5-60 minutes phosgene is slowly added to the heated mixture at such a rate that the temperature remains between 133° and 135° C. When the consumption of phosgene has ceased, the mixture is cooled and filtered to remove insoluble material. Finally, the solvent, alkyl isocyanate, and excess phosgene are evaporated, leaving the sulfonyl isocyanate (II).

If desired, the alkyl isocyanate-sulfonamide adduct can be made and isolated before reaction with the phosgene. In this case the sulfonamide (IV), alkyl isocyanate, and anhydrous base (e.g, K₂ CO₃) in a polar, aprotic solvent (e.g. acetone, butanone, or acetonitrile) are mixed and heated under reflux for 1 to 6 hours. The reaction mixture is then diluted with water, and the pH is adjusted to about 3 with acid (e.g. HCl, H₂ SO₄). The adduct is filtered out and dried, and then reacted with phosgene as described above. This procedure modification is especially useful when sulfonamide (IV) is high melting and has low solubility in the phosgenation solvent.

Sulfonyl isocyanates (II) can also be prepared by the following method. ##STR13##

The sulfonamide (IV) is heated at reflux in an excess of thionyl chloride. The reaction is continued until the sulfonamide protons are no longer detectable in the proton magnetic resonance spectrum. From 16 hours to 5 days is typically sufficient for complete conversion to the thionylamide (V) (Equation 3a).

The thionyl chloride is evaporated and the residue is treated with an inert solvent (e.g. toluene) containing at least one equivalent (typically 2-3 equivalents) of phosgene. A catalytic amount of pyridine (typically 0.1 equivalent) is added, and the mixture is heated to about 60°-140° C., with 80°-100° preferred. Conversion to the isocyanate (II) is usually substantially complete within 15 minutes to 3 hours (Equation 3b). The mixture is then cooled and filtered, and the solvent is evaporated, leaving the sulfonyl isocyanate (II).

Sulfonyl isothiocyanates (II, W is S) are known in the art and are prepared from the corresponding sulfonamides (IV) by reaction with carbon disulfide and potassium hydroxide followed by treatment of the resulting dipotassium salt VI with phosgene. Such a procedure is described in Arch. Pharm. 299, 174 (1966). ##STR14##

Many of the compounds of Formula I can be prepared by the procedure shown in Equation 5. ##STR15##

The reaction of Equation 5 is carried out by contacting phenylcarbamates or phenylthiocarbamates of Formula VII with aminoheterocycles of Formula III in an inert organic solvent such as dioxane or tetrahydrofuran at temperatures of about 20°-100° C. for a period of about one-half to twenty-four hours. The product can be isolated by evaporation of the reaction solvent and purified by methods previously described.

Phenylcarbamates and phenylthiocarbamates of Formula VII can be prepared by the methods described, or modifications thereof known to those skilled in the art, in U.S. Pat. No. 4,443,243.

Alternatively, many of the compounds of Formula I can be prepared by the method described in Equation 6. ##STR16##

The reaction of Equation 6 can be carried out by contacting equimolar amounts of a sulfonamide of Formula IV with a heterocyclic phenylcarbamate or phenylthiocarbamate of Formula VIII in the presence of a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), by methods analogous to those described in South African Patent Application 830441. The phenylcarbamates and phenylthiocarbamates of Formula VIII can be prepared by methods, or modifications thereof known to those skilled in the art, described in South African Patent Application No. 825671 and South African Patent Application No. 825045.

The sulfonamides of Formula IV can be prepared as shown in Equation 7. ##STR17##

Treatment of a condensed isothiazole-3(2H)-one-1,1-dioxide of Formula IX or a condensed 1,2-thiazine-3(2H)-one-1,1-dioxide of Formula XI with an appropriately substituted alcohol in the presence of an acid catalyst such as hydrogen chloride or para-toluenesulfonic acid gives sulfonamides IV. The reaction may be carried out at ambient to reflux temperature using excess alcohol as the solvent or in an inert solvent such as toluene or xylene.

The alcohols of Formula X are known or can be prepared by methods known in the art. In cases where R₁ is substituted with ##STR18## it is often more convenient to first prepare the corresponding sulfonamides (of Formula IV), sulfonylureas, or sulfonylthioureas (of Formula I) in which R₁ is substituted with one or two hydroxy groups. The hydroxy group (or groups) can then be functionalized to give the desired derivatives using methods which are well known in the art.

In the same way, when R₁ is substituted with ##STR19## it is often more convenient to first prepare the corresponding sulfonamides (of Formula IV), sulfonylureas, or sulfonylthioureas (of Formula I) in which R₁ is substituted with one or two mercapto groups. The mercapto group (or groups) can then be functionalized to give the desired derivatives using methods which are well known in the art.

It is expected that any derivative of an alcohol or thiol which is converted to the alcohol or thiol in a spray solution, on the plant surface, in plant tissue, or in the soil will give an effective herbicide when incorporated as a substituent on R₁.

When R₁ is substituted with one or two ##STR20## groups it is expected that derivatives wherein A is a heterocycle other than those described herein will also be effective herbicides.

When R₁ is substituted with one or two S(O)_(n) R₇ groups and n is equal to 1 or 2, the sulfonamides (of Formula IV), sulfonylureas and sulfonylthioureas (of Formula I) may also be prepared from the corresponding compounds in which n is equal to 0 by contact with an oxiding agent such as hydrogen peroxide or meta-chloroperbenzoic acid. The level of oxidation may be controlled by the amount of oxidant used and by the reaction temperture according to procedures which are known in the art.

Condensed isothiazole-3(2H)-one-1,1-dioxides of Formula IX and condensed 1,2-thiazine-3(2H)-one-1,1-dioxides of Formula XI are known or can be prepared by methods known in the art as shown in Equation 8. ##STR21##

Sulfonamides of Formulas XII and XIII where R₁₈ is a displaceable substituent such as alkoxy, aryloxy, halo, or hydroxy are cyclized to compounds of Formulas IX and XI under a variety of acidic and basic conditions (including those found in U.S. Pat. No. 4,430,355 (1984).

The sulfonamides of Formula XII and XIII can be prepared by methods which are known in the art. The benzenesulfonamides are disclosed in U.S. Pat. No. 4,394,506 (1983). The benzylsulfonamides are disclosed in U.S. Pat. No. 4,420,325 (1983). The thiophenesulfonamides are disclosed in European Patent Application No. 30,142 (published June 10, 1981). The indolesulfonamides are disclosed in European Patent Application No. 70,698 (published Jan. 26, 1983). The pyrazolesulfonamides are disclosed in European Patent Application No. 87,780 (published Sept. 7, 1983).

The heterocyclic amines of Formulae IIIa-IIIg below are either known or can be prepared by obvious methods by one skilled in the art. ##STR22##

For a review of the synthesis and reactions of 2-amino- and 2-methylaminopyrimidines IIIa (Z═CH) see The Chemistry of Heterocyclic Compounds, Vol. 16, Wiley-Interscience, New York (1962). For a review of the synthesis and reactions 2-amino- and 2-methylamino-s-triazines IIIa (Z═N) see The Chemistry of Heterocyclic Compounds, Vol. 13, Wiley-Interscience, New York (1959), F. C. Schaefer, U.S. Pat. No. 3,154,537 and F. C. Schaefer and K. R. Huffman J. Org. Chem., 28, 1812 (1963). The synthesis of the bicyclic amines IIIb and IIIc is taught in U.S. Pat. No. 4,339,267. The synthesis of bicyclic amines IIId is taught in U.S. Pat. No. 4,487,626. The preparation of aminomethyltriazines IIIf is taught in U.S. Pat. No. 4,496,392. The preparation off cyanopyridines and cyanopyrimidines IIIg is taught in European Publication No. 125,864 (published Nov. 21, 1984).

The amines of Formula III where X or X₁ Is OCF₂ H and/or Y is OCF₂ H or SCF₂ H can be prepared by methods taught in South African Patent Application No. 825,045, or by suitable modifications that would be obvious to one skilled in the art.

The pyrimidines of Formula IIIa (Z═CH) where Y is ##STR23## can be prepared according to the methods taught in European Patent Application No. 82306492.8 (Publication No. 84,224) or suitable modifications thereof known to one skilled in the art.

The triazoles of Formula IIIe can be prepared according to the methods taught in U.S. Pat. No. 4,421,550.

EXAMPLE 1 2-Aminosulfonylbenzoic acid, 2-hydroxyethyl ester

Hydrogen chloride gas was passed through a mixture of 54.9 g of saccharin and 500 ml of ethylene glycol for 11/2 hours. The mixture, which had warmed to 41° C., was then stirred at ambient temperature for 65 hours. The resulting solution was poured into 2 liters of ice water and the product extracted with ethyl acetate. The extracts were washed with water, dried (MgSO₄), and the solvent removed under reduced pressure to give a colorless oil which slowly crystallized. The white solid was triturated with n-butylchloride to give 44.9 g of the title compound, m.p. 84°-86.5° C.

IR (neat) 1720 cm⁻¹ (ester):

NMR (CDCl₃ /DMSO-d₆)δ: 3.8 (m, 2H, CH₂ OH); 4.4 (m, 2H, CO₂ CH₂ --); 5.15 (br, 1H, OH); 7.2 (br s, 2H, NH₂); and 7.6-8.2 (m, 4H, aromatics).

EXAMPLE 2 2-Aminosulfonfylbenzoic acid, 2-trimethylsilyloxyethyl ester

To a slurry of 12.25 g of 2-aminosulfonylbenzoic acid, 2-hydroxyethyl ester, 125 ml of dry methylene chloride, and 7.7 ml of triethylamine was added dropwise over 10 minutes 6.3 ml of trimethylsilyl chloride (exotherm to 36° C.). The resulting solution was allowed to stand at ambient temperature for 18 hours and then washed with saturated sodium chloride solution, dried (MgSO₄), and the solvent removed under reduced pressure to give an oil which was chromatographed on silica gel eluting with 25% EtOAc:hexane to give a colorless oil which slowly crystallized. Trituration with hexane gave 8.0 g of white crystals, m.p. 72°-76° C.

IR (nujol) 1738 cm⁻¹ (ester).

NMR (CDCl₃)δ: 0.1 (s, 9H, Si(CH₃)₃); 3.9 (m, 2H, --CH₂ OSiMe₃); 4.4 (m, 2H, CO₂ CH₂ --); 5.95 (br s, 2H, NH₂); and 7.4-8.2 (m, 4H, aromatics).

EXAMPLE 3 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester Method A

To a solution of 0.49 g of 2-aminosulfonylbenzoic acid, 2-hydroxyethyl ester and 0.49 g of 4,6-dimethylpyrimidin-2-yl-carbamic acid, phenyl ester in 10 ml of dry acetonitrile was added 0.30 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After stirring for 2 hours at ambient temperature the solution was diluted with 10 ml of water and acidified to pH 2 with 5% HCl. The solvent was removed under reduced pressure and the wet residue triturated with n-butyl chloride to give a white solid which was collected, washed thoroughly with n-butyl chloride and dried in vacuo. 0.6 g, m.p. 103°-107° C.(dec).

Method B

To a solution of 0.64 g of 2-aminosulfonylbenzoic acid, 2-trimethylsilyloxyethyl ester and 0.49 g of 4,6-dimethylpyrimidin-2-yl-carbamic acid, phenyl ester in 20 ml of acetonitrile was added 0.30 ml of DBU. After 1/2 hour the solvent was removed under reduced pressure, the residue dissolved in 25 ml of methylene chloride, washed with 5% NH₄ Cl, dried (MgSO₄), and the solvent removed under reduced pressure. The residue was triturated with ether to give 0.46 g of white solid, m.p. 102°-106° C.(dec). The NH₄ Cl wash was acidified to pH 1 with 5% HCl. extracted with methylene chloride, dried (MgSO₄), and the solvent removed under reduced pressure to give a white foam which was triturated with n-butylchloride to give an additional 0.23 g of the title compound, m.p. 110°-113° C.(d).

IR (nujol) 1730 cm⁻¹ (ester), 1715 cm⁻¹ (sulfonylurea).

NMR(CDCl₃)δ: 2.48 (s, 6H, CH₃ 's); 3.96 (m, 2H, CH₂ OH); 4.50 (m, 2H, CO₂ CH₂ --); 6.75 (s, 1H, pyr. C5--H); 7.66 (m, 3H, aromatics); 8.0 (br s, 1H, NH); 8.32 (m, 1H, aromatic); and 13.2 (br s, 1H, NH).

EXAMPLE 4 2-Aminosulfonylbenzoic acid, 2-methanesulfonyloxy ethyl ester

To a mixture of 12.25 g of 2-aminosulfonylbenzoic acid, 2-hydroxyethyl ester, 125 ml of dry methylene chloride, and 7.7 ml of triethylamine was added dropwise a solution of 3.9 ml of methanesulfonyl chloride in 25 ml of methylene chloride (exotherm to 37° C.). The resulting solution was allowed to stand for 18 hours and an additional 0.2 ml of methanesulfonyl chloride then added. After an additional 24 hours the reaction mixture was washed successively with water, 5% HCl, water, and saturated sodium chloride, dried (MgSO₄), and the solvent removed under reduced pressure to give a white solid which was triturated with n-butylchloride to give 8.0 g of the title compound, m.p. 124°-126° C.

IR (nujol) 1710 cm⁻¹ (ester).

NMR(CDCl₃)δ: 3.20 (s, 3H, OSO₂ CH₃); 4.53 (s, 4H, --CH₂ CH₂ --); 7.3 (br s, 2H, NH₂); and 7.7-8.1 (m, 4H, aromatics).

EXAMPLE 5 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-methanesulfonyloxy ester

To a solution of 0.65 g of 2-aminosulfonylbenzoic acid, 2-methanesulfonyloxyethyl ester, 0.55 g of 4,6-dimethoxypyrimidin-2-yl-carbamic acid, phenyl ester and 10 ml of dry acetonitrile was added 0.30 ml of DBU. After 1 hour the solution was diluted with 10 ml of water and acidified to pH 1 with 5% HCl. The white solid precipitate was collected, washed with water and then with ether to give 0.52 g, m.p. 118°-120° C.(dec).

IR(nujol): 1730 cm⁻¹ (ester), 1708 cm⁻¹ (sulfonylurea).

NMR(CDCl₃)δ: 3.05 (s, 3H, OSO₂ CH₃); 3.99 (s, 6H, OCH₃ 's); 4.55 (m, 4H, --CH₃ CH₂ --); 5.80 (s, 1H, pyr. C5--H); 7.35 (br s, 1H, NH); 7.75 (m, 3H, aromatics); 8.50 (m, 1H, aromatic); and 12.63 (br s, 1H, NH).

Using the procedures and examples shown above, one skilled in the art can prepare the compounds in Tables 1-20.

                                      TABLE 1                                      __________________________________________________________________________      ##STR24##                                                                     R.sub.1          X        Y        Z   m.p. (°C.)                       __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 CH.sub.3 CH  110-113 (d)                             CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 OCH.sub.3                                                                               CH   97-100 (d)                             CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               CH  123-126 (d)                             CH.sub.2 CH.sub.2 OH                                                                            Cl       OCH.sub.3                                                                               CH  124-127 (d)                             CH.sub.2 CH.sub.2 OH                                                                            Br       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               OCH.sub.2 CH.sub.3                                                                      CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OH                                                                            CF.sub. 3                                                                               CF.sub.3 CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 CH.sub.2 OCH.sub.3                                                                      CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               CH.sub.2 OCH.sub.3                                                                      CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CH.sub.2 F                                                                    CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OH                                                                            CH.sub.2 F                                                                              OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 CH.sub.3 N   144-146 (d)                             CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 OCH.sub.3                                                                               N   140-143 (d)                             CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               N   137-139 (d)                             CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               OCH.sub.2 CH.sub.3                                                                      N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CHF.sub.2                                                                     OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CF.sub.3                                                                      CH.sub.3 N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               NHCH.sub.3                                                                              N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               N(CH.sub.3).sub.2                                                                       N                                           CH.sub. 2 CH.sub.2 OH                                                                           OCH.sub.2 CH.sub.2 F                                                                    CH.sub.3 N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CF.sub.3                                                                      CH.sub.3 N                                           CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 OCH.sub.2 CCH                                                                           N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.3 CH.sub.3 CH  110-112 (d)                             CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.3 OCH.sub.3                                                                               CH  141-143 (d)                             CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               CH  150-152 (d)                             CH.sub.2 CH(OH)CH.sub.3                                                                         Cl       OCH.sub.3                                                                               CH  147-149 (d)                             CH.sub.2 CH(OH)CH.sub.3                                                                         Br       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.3 OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               OCH.sub.2 CH.sub.3                                                                      CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         CF.sub.3 CF.sub.3 CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.3 CH.sub.2 OCH.sub.3                                                                      CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               CH.sub.2 OCH.sub.3                                                                      CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CH.sub.2 F                                                                    CH.sub.3 CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.2 F                                                                              OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.3 CH.sub.3 N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.3 OCH.sub.3                                                                               N   147-150 (d)                             CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               N   142-144 (d)                             CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               OCH.sub.2 CH.sub.3                                                                      N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                               N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CHF.sub.2                                                                     OCH.sub.3                                                                               N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CF.sub.3                                                                      CH.sub.3 N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               NHCH.sub.3                                                                              N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.3                                                                               N(CH.sub.3).sub.2                                                                       N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CH.sub.2 F                                                                    CH.sub.3 N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         OCH.sub.2 CF.sub.3                                                                      CH.sub.3 N                                           CH.sub.2 CH(OH)CH.sub.3                                                                         CH.sub.3 OCH.sub.2 CCH                                                                           N                                           CH(CH.sub.3)CH.sub.2 OH                                                                         CH.sub.3 CH.sub.3 CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         CH.sub.3 OCH.sub.3                                                                               CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         Cl       OCH.sub.3                                                                               CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         Br       OCH.sub.3                                                                               CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         CH.sub.3 OCF.sub.2 H                                                                             CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.3)CH.sub.2 OH                                                                         CH.sub.3 CH.sub.3 N                                           CH(CH.sub.3)CH.sub.2 OH                                                                         CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.3)CH.sub.2 OH                                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH(CH.sub.3)CH.sub.2 OH                                                                         OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH(CH.sub.3)CH.sub.2 OH                                                                         OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   CH.sub.3 CH.sub.3 CH  112-116 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   CH.sub.3 OCH.sub.3                                                                               CH  109-114 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH  139-141 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   Cl       OCH.sub.3                                                                               CH  127-131 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   Br       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   CH.sub.3 OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   CH.sub.3 CH.sub.3 N   147-148 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   CH.sub.3 OCH.sub.3                                                                               N   136-139 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N   131-134 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CH.sub.2 CH(OH)CH.sub.2 CH.sub.3                                                                CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(OH)CH.sub.2 CH.sub.3                                                                CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.2 CH.sub.3                                                                OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH(CH.sub.2 OH)CH.sub.2 CH.sub.3                                                                Cl       OCH.sub.3                                                                               CH                                          CH(CH.sub.2 OH)CH.sub.2 CH.sub.3                                                                Br       OCH.sub.3                                                                               CH                                          CH(CH.sub.2 OH)CH.sub.2 CH.sub.3                                                                CH.sub.3 OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                                OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                                OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                                OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.3)CH.sub.2 CH.sub.2 OH                                                                CH.sub.3 CH.sub.3 N                                           CH(CH.sub.3)CH.sub.2 CH.sub.2 OH                                                                CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.3)CH.sub.2 CH.sub.2 OH                                                                OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                          OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                          OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                                CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                                CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                                OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                                Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.3).sub.2 OH                                                                  Br       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.3 OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH(OH)CH.sub.2 CH.sub.2 CH.sub.3                                                       OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH(OH)CH.sub.2 CH.sub.2 CH.sub.3                                                       OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH(CH.sub.2 OH)CH.sub.2 CH.sub.2 CH.sub.3                                                       OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.2 OH)CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.3 CH.sub.3 N                                           CH(CH.sub.2 OH)CH.sub.2 CH.sub.2 CH.sub.3                                                       CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 CH.sub.3                                                       OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 CH.sub.3                                                       OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 CH.sub.3                                                       OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CH(CH.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 OH                                                       CH.sub.3 CH.sub.3 CH                                          CH(CH.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 OH                                                       CH.sub.3 OCH.sub.3                                                                               CH                                          CH(CH.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 OH                                                       OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                       Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                       Br       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                       CH.sub.3 OCF.sub.2 H                                                                             CH                                          CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2 OH                                                       OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2 OH                                                       OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2 OH                                                       OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 C(CH.sub.3)(OH)CH.sub.2 CH.sub.3                                                       CH.sub.3 CH.sub.3 N                                           CH.sub.2 CH(CH.sub.3)CH(OH)CH.sub.3                                                             CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH(CH.sub.3)CH(OH)CH.sub.3                                                             OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH(CH.sub.3)CH(CH.sub.3)CH.sub.2 OH                                                             OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH(CH.sub.3)CH(CH.sub.3)CH.sub.2 OH                                                             OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CHCH(CH.sub.3)CH.sub.2 CH.sub.2 OH                                                              CH.sub.3 OCH.sub.3                                                                               N                                           CHCH(CH.sub.3)CH.sub.2 CH.sub.2 OH                                                              CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                       CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                       OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.2 OH)CH.sub.2 CH.sub.3                                                       Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.2 OH)CH.sub.2 CH.sub.3                                                       Br       OCH.sub.3                                                                               CH                                          CHC(CH.sub.3).sub.2 CH.sub.2 OH                                                                 CH.sub.3 OCF.sub.2 H                                                                             CH                                          CHC(CH.sub.3).sub.2 CH.sub.2 OH                                                                 OCH.sub.3                                                                               OCF.sub.2 H                                                                             CH                                          CH.sub.2 CH(CH.sub.3)CH(OH)CH.sub.3                                                             OCF.sub.2 H                                                                             OCF.sub.2 H                                                                             CH                                          CH(CH.sub.3)CH(CH.sub.3)CH.sub.2 OH                                                             OCH.sub.3                                                                               CH(OCH.sub. 3).sub.2                                                                    CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 OH                                                       CH.sub.3 CH.sub.3 N                                           CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                       CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH(OH)CH(CH.sub.3).sub.2                                                               OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH(CH.sub.2 OH)CH(CH.sub.3).sub.2                                                               OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 OH                                                       OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CH.sub.2 CHCHCH.sub.2 OH                                                                        CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CHCHCH.sub.2 OH                                                                        CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CHCHCH.sub.2 OH                                                                        OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CHCH.sub.2                                                                       Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CHCH.sub.2                                                                       OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.2 OH)CHCH.sub.2                                                                       CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.2 OH)CHCH.sub.2                                                                       OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CCCH.sub.2 OH                                                                          CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CCCH.sub.2 OH                                                                          CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CCCH.sub.2 OH                                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CCH                                                                              Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CCH                                                                              OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.2 OH)CCH                                                                              CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.2 OH)CCH                                                                              OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            CH.sub.3 CH.sub.3 CH  152-155 (d)                             CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            CH.sub.3 OCH.sub.3                                                                               CH   91-95 (d)                              CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               CH  118-120 (d)                             CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            Cl       OCH.sub.3                                                                               CH   96-100 (d)                             CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            CH.sub.3 OCH.sub.3                                                                               N   151-153 (d)                             CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               N   141-151 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub. 3                                                  CH.sub.3 CH.sub.3 CH  152-155 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                   CH.sub.3 OCH.sub.3                                                                               CH  131-135 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH  103-106 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                   Cl       OCH.sub.3                                                                               CH  136-138 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                   OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                   CH.sub.3 OCH.sub.3                                                                               N   151-153.5 (d)                           CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N   145-147 (d)                             CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                         CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                         CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                         Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                         OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                         CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH(OSO.sub.2 CH.sub.3 )CH.sub.3                                                        OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.3                                                CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.3                                                CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.3                                                OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.2 OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                                       CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.2)CH.sub.2 OSO.sub.2 CH.sub.3                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.3                                                CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.3                                                CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.3                                                OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.2 OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.                                        CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.2 OSO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                                       OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                   CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                   CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                   OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                   CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                          CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                          CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                          Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                          OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                          OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                  CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                  CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                  OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                  Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                  OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                  CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                  OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 -p-C.sub.6 H.sub.4 CH.sub.3                                         CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OSO.sub.2  -p-C.sub.6 H.sub.4 CH.sub.3                                        CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub. 2 OSO.sub.2 -p-C.sub.6 H.sub.4 CH.sub.3                                        OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 -p-C.sub.6 H.sub.4 CH.sub.3                                         Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 -p-C.sub.6 H.sub.4 CH.sub.3                                         OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 -p-C.sub.6 H.sub.4 CH.sub.3                                         CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 -p-C.sub.6 H.sub.4 CH.sub.3                                         OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                   CH.sub.3 CH.sub.3 CH  160-162 (d)                             CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                   CH.sub.3 OCH.sub.3                                                                               CH  162-164 (d)                             CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH  119-122 (d)                             CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                   OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                   CH.sub.3 OCH.sub.3                                                                               N   128-131 (d)                             CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N   140-141.5 (d)                           CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                            CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                            CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                            Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                            CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                          CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                          Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                          OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                                   CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OSO.sub. 2 N(CH.sub.3).sub.2                                                  CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                                   OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                                   CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                           CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                           CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                           OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                           Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                           OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                           CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                           OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SOCH.sub.3                                                                    CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 SOCH.sub.3                                                                    CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SOCH.sub.3                                                                    OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SOCH.sub.3                                                                    Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SOCH.sub.3                                                                    OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 SOCH.sub.3                                                                    CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SOCH.sub.3                                                                    OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                             CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                             CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                             OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                             Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                             OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                             CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                             OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                   CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                   CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                   OCH.sub.3                                                                               CH(OCH.sub. 3).sub.2                                                                    CH                                          CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                   CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                          CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                          CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                          Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                          OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                            CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                            CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                            Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                            OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                            CH.sub. 3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                                 CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                                 CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                                 Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                                 OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                                 CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                                 CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                                 CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                                 Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                                 OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                                 CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                          CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub. 2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                          Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                          OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OPS(OCH.sub.3).sub.2                                                          CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OPS(OCH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPS(OCH.sub.3).sub.2                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPS(OCH.sub.3).sub.2                                                          Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPS(OCH.sub.3).sub.2                                                          OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OPS(OCH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OPS(OCH.sub.3).sub.2                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5                                                     CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5                                                     CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5                                                     OCH.sub.3                                                                               OCH.sub. 3                                                                              CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5                                                     Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5                                                     OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5                                                     CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCO.sub.2 C.sub.6 H.sub.5                                                     OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH(OH)CH.sub.2 OH                                                                      CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(OH)CH.sub.2 OH                                                                      CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.2 OH                                                                      OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.2 OH                                                                      Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(OH)CH.sub.2 OH                                                                      OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH.sub.2 CH(OH)CH.sub.2 OH                                                                      CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH(OH)CH.sub.2 OH                                                                      OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH(CH.sub.2 OH).sub.2                                                                           CH.sub.3 CH.sub.3 CH                                          CH(CH.sub.2 OH).sub.2                                                                           CH.sub.3 OCH.sub.3                                                                               CH                                          CH(CH.sub.2 OH).sub.2                                                                           OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH(CH.sub.2 OH).sub.2                                                                           Cl       OCH.sub.3                                                                               CH                                          CH(CH.sub.2 OH).sub.2                                                                           OCH.sub.3                                                                               CH(OCH.sub.3).sub.2                                                                     CH                                          CH(CH.sub.2 OH).sub.2                                                                           CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.2 OH).sub.2                                                                           OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            CH.sub.3 CH.sub.3 N   150-153 (d)                             CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                   CH.sub.3 CH.sub.3 N   158.5-160 (d)                           CH.sub.2 CH.sub.2 OPO(OCH.sub.2 CH.sub.3).sub.2                                                 CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.2 CH.sub.3).sub.2                                                 CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.2 CH.sub.3).sub.2                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.2 CH.sub.3).sub.2                                                 Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OPO(OCH.sub.2 CH.sub.3).sub.2                                                 CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OPO(OCH.sub.2 CH.sub.3).sub.2                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 CH.sub.3 OCH.sub.3                                                                               CH   79-82 (d)                              CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               CH  wax                                     CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 Cl       OCH.sub.3                                                                               CH  wax                                     CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 CH.sub.3 OCH.sub.3                                                                               N   oil                                     CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 OCH.sub.3                                                                               OCH.sub.3                                                                               N   wax                                     CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                         CH.sub.3 CH.sub.3 CH                                          CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                         CH.sub.3 OCH.sub.3                                                                               CH                                          CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                         Cl       OCH.sub.3                                                                               CH                                          CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                         CH.sub.3 OCH.sub.3                                                                               N                                           CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N   132-135 (d)                             CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N   144-146 (d)                             CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                     CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                     CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                     OCH.sub.3                                                                               OCH.sub.3                                                                               CH  133-135 (d)                             CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                     Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                     CH.sub.3 OCH.sub.3                                                                               N   118-121 (d)                             CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                     OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5                                                     OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CH.sub.2 CH.sub.2 OCONH.sub.2                                                                   CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCONH.sub.2                                                                   CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCONH.sub.2                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCONH.sub.2                                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCONH.sub.2                                                                   CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCONH.sub.2                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2  -p-ClC.sub.6 H.sub.4                                               OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2  -p-ClC.sub.6 H.sub.4                                               CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2 .sub.--m-ClC.sub.6 H.sub.4                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2 .sub.--m-ClC.sub.6 H.sub.4                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OCH.sub.2  -o-ClC.sub.6 H.sub.4                                               OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 OCH.sub.2  -o-ClC.sub.6 H.sub.4                                               CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SH                                                                            CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 SH                                                                            CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SH                                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SH                                                                            Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SH                                                                            CH.sub.3 CH.sub.3 N                                           CH.sub.2 CH.sub.2 SH                                                                            CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SH                                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SH                                                                            OCH.sub.2 CH.sub.3                                                                      NHCH.sub.3                                                                              N                                           CH.sub.2 CH.sub.2 SH                                                                            OCH.sub.3                                                                               N(CH.sub.3).sub.2                                                                       N                                           CH.sub.2 CH(SH)CH.sub.3                                                                         CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(SH)CH.sub.3                                                                         CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(SH)CH.sub.3                                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(SH)CH.sub.3                                                                         Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(SH)CH.sub.3                                                                         CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH(SH)CH.sub.3                                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH.sub.2 SH                                                                   CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 CH.sub.2 SH                                                                   CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH.sub.2 SH                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH.sub.2 SH                                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 CH.sub.2 SH                                                                   CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 CH.sub.2 SH                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH(SH)CH.sub.2 SH                                                                      CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH(SH)CH.sub.2 SH                                                                      CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH(SH)CH.sub.2 SH                                                                      OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH(SH)CH.sub.2 SH                                                                      Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH(SH)CH.sub.2 SH                                                                      CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH(SH)CH.sub.2 SH                                                                      OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                   CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                   CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                   CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCOCH.sub.2 CH.sub.3                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub. 2 SCOCH.sub.2 CH.sub.2 CH.sub.3                                                OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCOCH(CH.sub.3).sub.2                                                         OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCO.sub.2 CH.sub.3                                                            CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 SCO.sub.2 CH.sub.3                                                            CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCO.sub.2 CH.sub.3                                                            Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCO.sub.2 CH.sub.3                                                            CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCO.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCO.sub.2 C.sub.6 H.sub.5                                                     OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCO.sub.2 C.sub.6 H.sub.5                                                     CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCON(CH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCON(CH.sub.3).sub.2                                                          OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCON(CH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCONH.sub.2                                                                   CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 SCONH.sub.2                                                                   CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCONH.sub.2                                                                   OCH.sub. 3                                                                              OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCONH.sub.2                                                                   Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SCONH.sub.2                                                                   CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SCONH.sub.2                                                                   OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SP(O)(OCH.sub.2 CH.sub.3).sub.2                                               CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 SP(O)(OCH.sub.2 CH.sub.3).sub.2                                               CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SP(O)(OCH.sub.2 CH.sub.3).sub.2                                               OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SP(O)(OCH.sub.2 CH.sub.3).sub.2                                               Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SP(O)(OCH.sub.2 CH.sub.3).sub.2                                               CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SP(O)(OCH.sub.2 CH.sub.3).sub.2                                               OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SP(S)(OCH.sub.3).sub.2                                                        CH.sub.3 CH.sub.3 CH                                          CH.sub.2 CH.sub.2 SP(S)(OCH.sub.3).sub.2                                                        CH.sub.3 OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SP(S)(OCH.sub.3).sub.2                                                        OCH.sub.3                                                                               OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SP(S)(OCH.sub.3).sub.2                                                        Cl       OCH.sub.3                                                                               CH                                          CH.sub.2 CH.sub.2 SP(S)(OCH.sub.3).sub.2                                                        CH.sub.3 OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 SP(S)(OCH.sub.3).sub.2                                                        OCH.sub.3                                                                               OCH.sub.3                                                                               N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               NH.sub.2 CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               NH.sub.2 N                                           CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.3                                                             CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               CH.sub.2 OCH.sub.2 CH.sub.3                                                             CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               CH.sub.2 OCH.sub.2 CH.sub.3                                                             N                                           CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 cyclopropyl                                                                             CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               cyclopropyl                                                                             CH                                          CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 cyclopropyl                                                                             N                                           CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               cyclopropyl                                                                             N                                           CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 CH.sub.2 SCH.sub.3                                                                      CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               CH.sub.2 SCH.sub.3                                                                      CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               CH.sub.2 SOCH.sub.3                                                                     CH                                          CH.sub.2 CH.sub.2 OH                                                                            CH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3                                                              CH                                          CH.sub.2 CH.sub.2 OH                                                                            OCH.sub.3                                                                               CH.sub.2 SO.sub.2 CH.sub.3                                                              CH                                          __________________________________________________________________________

                  TABLE 2                                                          ______________________________________                                          ##STR25##                                                                                                           m.p.                                     R.sub.1     R.sub.2  X       Y        Z(°C.)                            ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                       H        CH.sub.3                                                                               CH.sub.3 CH                                       CH.sub.2 CH.sub.2 OH                                                                       H        CH.sub.3                                                                               OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OH                                                                       H        OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OH                                                                       H        Cl      OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OH                                                                       H        OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                       CH.sub.2 CH.sub.2 OH                                                                       H        CH.sub.3                                                                               OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 OH                                                                       H        OCH.sub.3                                                                              OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H        CH.sub.3                                                                               CH.sub.3 CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H        CH.sub.3                                                                               OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub. 2 OSO.sub.2 CH.sub.3                                                      H        OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H        Cl      OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H        OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H        CH.sub.3                                                                               OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H        OCH.sub.3                                                                              OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 OH                                                                       3-Cl     CH.sub.3                                                                               CH.sub.3 CH                                       CH.sub.2 CH.sub.2 OH                                                                       6-Cl     CH.sub.3                                                                               OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OH                                                                       5-CF.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OH                                                                       5-CH.sub.3                                                                              Cl      OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OH                                                                       5-SCH.sub.3                                                                             OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                       CH.sub.2 CH.sub.2 OH                                                                       5-OCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 OH                                                                       3-CH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-C.sub.2 H.sub.5                                                                       CH.sub.3                                                                               CH.sub.3 CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-F      CH.sub.3                                                                               OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-Br     OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-OCF.sub.2 H                                                                           Cl      OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-SCF.sub.2 H                                                                           OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-OCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-OCH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 SH                                                                       H        CH.sub.3                                                                               OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 SH                                                                       H        OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                       CH.sub.2 CH.sub.2 SH                                                                       H        CH.sub.3                                                                               OCH.sub.3                                                                               N                                        CH.sub.2 CH.sub.2 SH                                                                       H        OCH.sub.3                                                                              OCH.sub.3                                                                               N                                        ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR26##                                                                                                          m.p.                                      R.sub.1     R.sub.2    XY            Z(°C.)                             ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3 CH.sub.3                                                                            CH                                        CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3 OCH.sub.3                                                                           CH                                        CH.sub.2 CH.sub.2 OH                                                                       H          OCH.sub.3 OCH.sub.3                                                                          CH                                        CH.sub.2 CH.sub.2 OH                                                                       H          ClOCH.sub.3   CH                                        CH.sub.2 CH.sub.2 OH                                                                       H          OCH.sub.3 CH(OCH.sub.3).sub.2                                                                CH                                        CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OH                                                                       H          OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          CH.sub.3 CH.sub.3                                                                            CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          CH.sub.3 OCH.sub.3                                                                           CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          OCH.sub.3 OCH.sub.3                                                                          CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          ClOCH.sub.3   CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          OCH.sub.3 CH(OCH.sub.3).sub.2                                                                CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 OH                                                                       3-Cl       CH.sub.3 CH.sub.3                                                                            CH                                        CH.sub.2 CH.sub.2 OH                                                                       3-Cl       CH.sub.3 OCH.sub.3                                                                           CH                                        CH.sub.2 CH.sub.2 OH                                                                       6-Cl       OCH.sub.3 OCH.sub.3                                                                          CH                                        CH.sub.2 CH.sub.2 OH                                                                       5-Cl       ClOCH.sub.3   CH                                        CH.sub.2 CH.sub.2 OH                                                                       5-CF.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2                                                                CH                                        CH.sub.2 CH.sub.2 OH                                                                       5-OCH.sub.3                                                                               CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OH                                                                       5-OCH.sub.3                                                                               OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-Cl       CH.sub.3 CH.sub.3                                                                            CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-Cl       CH.sub.3 OCH.sub.3                                                                           CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-CH.sub.3 OCH.sub.3 OCH.sub.3                                                                          CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-CH.sub.3 ClOCH.sub.3   CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-CH.sub.3 OCH.sub.3 CH(OCH.sub.3).sub.2                                                                CH                                        CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-OCH.sub.3                                                                               CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-OCH.sub.3                                                                               OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 OH                                                                       5-SCH.sub.3                                                                               CH.sub.3 OCH.sub.3                                                                           CH                                        CH.sub.2 CH.sub.2 OH                                                                       5-SCH.sub.3                                                                               OCH.sub.3 OCH.sub.3                                                                          CH                                        CH.sub.2 CH.sub.2 OH                                                                       5-SCH.sub.3                                                                               CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OH                                                                       5-SCH.sub.3                                                                               OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 OH                                                                       5-Cl       CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OH                                                                       5-Cl       OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 OH                                                                       5-CH.sub.2 OCH.sub.3                                                                      CH.sub.3 OCH.sub.3                                                                           CH                                        CH.sub.2 CH.sub.2 OH                                                                       5-CH.sub.2 OCH.sub.3                                                                      OCH.sub.3 OCH.sub.3                                                                          CH                                        CH.sub.2 CH.sub.2 OH                                                                       5-CH.sub.2 OCH.sub.3                                                                      CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub. 2 CH.sub.2 OH                                                                      5-CH.sub.2 OCH.sub.3                                                                      OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-Cl       CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-SCH.sub.3                                                                               CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       5-SCH.sub.3                                                                               OCH.sub.3 OCH.sub.3                                                                          N                                         CH.sub.2 CH.sub.2 SH                                                                       H          CH.sub.3 OCH.sub.3                                                                           CH                                        CH.sub.2 CH.sub.2 SH                                                                       H          OCH.sub.3 OCH.sub.3                                                                          CH                                        CH.sub.2 CH.sub.2 SH                                                                       H          ClOCH.sub.3   CH                                        CH.sub.2 CH.sub.2 SH                                                                       H          CH.sub.3 OCH.sub.3                                                                           N                                         CH.sub.2 CH.sub.2 SH                                                                       H          OCH.sub.3 OCH.sub.3                                                                          N                                         ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR27##                                                                                                             m.p.                                   R.sub.1       R.sub.2   X.sub.1   Y.sub.1                                                                              (°C.)                           ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                         H         CH.sub.3  O                                            CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.3 O                                            CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.2 CH.sub.3                                                                       O                                            CH.sub.2 CH.sub.2 OH                                                                         H         OCF.sub.2 H                                                                              O                                            CH.sub.2 CH.sub.2 OH                                                                         H         CH.sub.3  CH.sub.2                                     CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.3 CH.sub.2                                     CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.2 CH.sub.3                                                                       CH.sub.2                                     CH.sub.2 CH.sub.2 OH                                                                         H         OCF.sub.2 H                                                                              CH.sub.2                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         CH.sub.3  O                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.3 O                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.2 CH.sub.3                                                                       O                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCF.sub.2 H                                                                              O                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         CH.sub.3  CH.sub.2                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.3 CH.sub.2                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.2 CH.sub.3                                                                       CH.sub.2                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCF.sub.2 H                                                                              CH.sub.2                                     CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                H         CH.sub.3  O                                            CH.sub.2 CH(OH)CH.sub.3                                                                      H         CH.sub.3  O                                            CH(CH.sub.3)CH.sub.2 OH                                                                      H         CH.sub.3  O                                            CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                              H         CH.sub.3  O                                            CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                              H         OCH.sub.3 O                                            CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                              H         OCH.sub.3 O                                            CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                      H         OCH.sub.3 O                                            CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                      H         OCH.sub.3 O                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         3-Cl      OCH.sub.3 O                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         5-Cl      OCH.sub.3 O                                            CH.sub.2 CH.sub.2 OH                                                                         6-Cl      OCH.sub.3 O                                            CH.sub.2 CH.sub.2 OH                                                                         5-OCH.sub.3                                                                              OCH.sub.3 O                                            CH.sub.2 CH.sub.2 SH                                                                         H         CH.sub.3  O                                            CH.sub.2 CH.sub.2 SH                                                                         H         OCH.sub.3 O                                            CH.sub.2 CH.sub.2 SH                                                                         H         OCH.sub.2 CH.sub.3                                                                       O                                            ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR28##                                                                     R.sub.1       R.sub.2   X.sub.1    m.p. (°C.)                           ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                         H         CH.sub.3                                               CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.3                                              CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.2 CH.sub.3                                     CH.sub.2 CH.sub.2 OH                                                                         H         OCF.sub.2 H                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         CH.sub.3                                               CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.3                                              CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.2 CH.sub.3                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCF.sub.2 H                                            CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                              5-Cl      OCH.sub.3                                              CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                              5-OCH.sub.3                                                                              OCH.sub.3                                              CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                        H         OCH.sub.3                                              CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                H         OCH.sub. 3                                             CH.sub.2 CH.sub.2 SH                                                                         H         CH.sub.3                                               CH.sub.2 CH.sub.2 SH                                                                         H         OCH.sub.3                                              ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR29##                                                                                                             m.p.                                   R.sub.1       R.sub.2   X.sub.1   Y.sub.3                                                                              (°C.)                           ______________________________________                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         CH.sub.3  H                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.3 H                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.2 CH.sub.3                                                                       H                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCF.sub.2 H                                                                              H                                            CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         CH.sub.3  CH.sub.3                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.3 CH.sub.3                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCH.sub.2 CH.sub.3                                                                       CH.sub.3                                     CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H         OCF.sub.2 H                                                                              CH.sub.3                                     CH.sub.2 CH.sub.2 OH                                                                         H         CH.sub.3  H                                            CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.3 H                                            CH.sub.2 CH.sub.2 OH                                                                         H         OCH.sub.3 CH.sub.3                                     CH.sub.2 CH.sub.2 OH                                                                         H         CH.sub.3  CH.sub.3                                     CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                       H         CH.sub.3  H                                            CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                H         OCH.sub.3 H                                            CH.sub.2 CH(OH)CH.sub.2 OH                                                                   5-Cl      OCH.sub.3 H                                            CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                      5-OCH.sub.3                                                                              OCH.sub.3 CH.sub.3                                     CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                          6-Cl      CH.sub.3  H                                            CH.sub.2 CH.sub.2 SOCH.sub.3                                                                 3-Cl      CH.sub.3  CH.sub.3                                     CH.sub.2 CH.sub.2 SH                                                                         H         CH.sub.3  H                                            CH.sub.2 CH.sub.2 SH                                                                         H         CH.sub.3  CH.sub.3                                     CH.sub.2 CH.sub.2 SH                                                                         H         OCH.sub.3 H                                            CH.sub.2 CH.sub.2 SH                                                                         H         OCH.sub.3 CH.sub.3                                     ______________________________________                                    

                                      TABLE 7                                      __________________________________________________________________________      ##STR30##                                                                                                         m.p.                                       R.sub.1           R.sub.2                                                                              X.sub.2                                                                             Y.sub.2                                                                               (°C.)                               __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                             H     CH.sub.3                                                                            OCH.sub.3                                         CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                    H     CH.sub.2 CH.sub.3                                                                   OCH.sub.3                                         CH.sub.2 CH(OH)CH.sub.3                                                                          H     CH.sub.2 CF.sub.3                                                                   OCH.sub.3                                         CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                          H     CH.sub.3                                                                            OCH.sub.2 CH.sub.3                                CH.sub.2 CH(OH)CH.sub.2 OH                                                                       H     CH.sub.2 CH.sub.3                                                                   OCH.sub.2 CH.sub.3                                CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                       H     CH.sub.2 CF.sub.3                                                                   OCH.sub.2 CH.sub.3                                CH(CHOH).sub.2    H     CH.sub.3                                                                            SCH.sub.3                                         CH(CH.sub.3)CH.sub.2 CH.sub.2 OH                                                                 H     CH.sub.2 CH.sub.3                                                                   SCH.sub.3                                         CH.sub.2 CH.sub.2 SOCH.sub.3                                                                     H     CH.sub.2 CF.sub.3                                                                   SCH.sub.3                                         CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                    H     CH.sub.3                                                                            SCH.sub.2 CH.sub.3                                CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 F                                                           H     CH.sub.2 CH.sub.3                                                                   SCH.sub.2 CH.sub.3                                CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                           H     CH.sub.2 CF.sub.3                                                                   SCH.sub.2 CH.sub.3                                CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                                    H     CH.sub.3                                                                            CH.sub.3                                          CH.sub.2 CH.sub.2 Si(CH.sub.3).sub.2 C.sub.6 H.sub.5                                             H     CH.sub.2 CH.sub.3                                                                   CH.sub.3                                          CH.sub.2 CH.sub.2 OH                                                                             H     CH.sub.2 CF.sub.3                                                                   CH.sub.3                                          CH.sub.2 CH.sub.2 OH                                                                             H     CH.sub.3                                                                            CH.sub.2 CH.sub.3                                 CH.sub.2 CH.sub.2 OH                                                                             H     CH.sub.2 CH.sub.3                                                                   CH.sub.2 CH.sub.3                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                    H     CH.sub.2 CF.sub.3                                                                   CH.sub.2 CH.sub.3                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH(CH.sub.3).sub.2                                                   H     CH.sub.3                                                                            OCH.sub.3                                         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                           H     CH.sub.2 CH.sub.3                                                                   OCH.sub.3                                         CH.sub.2 CCCH.sub.2 OH                                                                           H     CH.sub.2 CF.sub.3                                                                   OCH.sub.3                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                             H     CH.sub.3                                                                            OCH.sub.3                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                             5-OCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                             5-Cl  CH.sub.3                                                                            OCH.sub.3                                         CH.sub.2 CH.sub.2 SH                                                                             H     CH.sub.3                                                                            OCH.sub.3                                         __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________      ##STR31##                                                                     R.sub.1      R.sub.3                                                                             X    Y      Z  m.p. (°C.)                             __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                        H    CH.sub.3                                                                            CH.sub.3                                                                              CH                                               CH.sub.2 CH.sub.2 OH                                                                        H    CH.sub.3                                                                            OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 OH                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 OH                                                                        H    Cl   OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 OH                                                                        H    OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                               CH.sub.2 CH.sub.2 OH                                                                        H    CH.sub.3                                                                            OCH.sub.3                                                                             N                                                CH.sub.2 CH.sub.2 OH                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H    CH.sub.3                                                                            CH.sub.3                                                                              CH                                               CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H    CH.sub.3                                                                            OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H    OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H    Cl   OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H    OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                               CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H    CH.sub.3                                                                            OCH.sub.3                                                                             N                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H    OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                CH.sub.2 CH.sub.2 OH                                                                        3-Cl CH.sub.3                                                                            CH.sub.3                                                                              CH                                               CH.sub.2 CH(OH)CH.sub.3                                                                     5-F  CH.sub.3                                                                            OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                               5-Cl OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                               CH(CHOH).sub.2                                                                              5-CH.sub.3                                                                          Cl   OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                            5-OCH.sub.3                                                                         OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                               CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                         6-Cl CH.sub.3                                                                            OCH.sub.3                                                                             N                                                CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                             H    OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                CH.sub.2 CH.sub.2 OCF.sub.2 H                                                               H    CH.sub.3                                                                            CH.sub.3                                                                              CH                                               CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                        H    CH.sub.3                                                                            OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 OCF.sub.2 H                                                               H    OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                               CH.sub.2 CH.sub.2 SOCH.sub.3                                                                H    Cl   OCH.sub.3                                                                             CH                                               CH.sub. 2 CH.sub.2 OSO.sub.2 N(CH.sub.3).sub.2                                              H    OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                               CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                     H    CH.sub.3                                                                            OCH.sub.3                                                                             N                                                CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                     H    OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                CH.sub.2 CH.sub.2 SH                                                                        H    OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                               __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________      ##STR32##                                                                     R.sub.1      R.sub.16                                                                           X    Y      Z   m.p. (°C.)                             __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                        H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                               H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                               H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                               H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH(OH)CH.sub.3                                                                     H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                     H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH(CH.sub.2 OH)CH.sub.3                                                                     H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH(CH.sub.2 OSO.sub.2 CH.sub.3)CH.sub.3                                                     H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OCF.sub.2 H                                                               H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OCF.sub.2 H                                                               H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                         H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                             H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                      H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                               H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                      H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-Cl                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-Cl                                                                               CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-F CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        5-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        5-Cl                                                                               CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        5-F CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        4-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        4-Cl                                                                               CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 SH                                                                        H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 SH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR33##                                                                     R.sub.1      R.sub.16                                                                           X    Y      Z   m.p. (°C.)                             __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                        H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH.sub.2 CH.sub.2 OH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                               H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                               H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                               H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH(OH)CH.sub.3                                                                     H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                     H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH(CH.sub.2 OH)CH.sub.3                                                                     H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH(CH.sub.2 OSO.sub.2 CH.sub.3)CH.sub.3                                                     H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OCF.sub.2 H                                                               H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OCF.sub.2 H                                                               H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                         H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                             H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                      H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                   CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                               H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                      H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-Cl                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OH                                                                        4-Cl                                                                               CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        4-F CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        5-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        5-Cl                                                                               CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OH                                                                        5-F CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        4-CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        4-CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        4-Cl                                                                               CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 SH                                                                        H   CH.sub.3                                                                            CH.sub.3                                                                              CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   Cl   OCH.sub.3                                                                             CH                                                CH.sub.2 CH.sub.2 SH                                                                        H   CH.sub.3                                                                            OCH.sub.3                                                                             N                                                 CH.sub.2 CH.sub.2 SH                                                                        H   OCH.sub.3                                                                           OCH.sub.3                                                                             N                                                 __________________________________________________________________________

                  TABLE 11                                                         ______________________________________                                          ##STR34##                                                                                                            m.p.                                    R.sub.1       R.sub.16                                                                               X       Y        Z (°C.)                          ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                         H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH(OH)CH.sub.3                                                                      H       Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                      H       OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH(CH.sub.2 OH)CH.sub.3                                                                      H       CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH(CH.sub.2 OSO.sub.2 CH.sub.3)CH.sub.3                                                      H       OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                          H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                              H       Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                       H       OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                H       CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                       H       OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         2-CH.sub.3                                                                             CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 OH                                                                         2-CH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         2-CH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         2-CH.sub.3                                                                             Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         2-CH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         2-CH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         2-Cl    OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         2-Cl    CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         2-F     CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         5-CH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         5-Cl    CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         5-F     CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub. 2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        2-CH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         2-CH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         2-Cl    CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 SH                                                                         H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 SH                                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         H       Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 SH                                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       ______________________________________                                    

                  TABLE 12                                                         ______________________________________                                          ##STR35##                                                                                                            m.p.                                    R.sub.1       R.sub.4 X       Y        Z (°C.)                          ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                         H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         H       Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OH                                                                         CH.sub.3                                                                               OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH.sub.2 CH.sub.2 OH                                                                         CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OH                                                                         CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         CH.sub.3                                                                               Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         CH.sub.3                                                                               OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH(OH)CH.sub.3                                                                      CH.sub.3                                                                               Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                      CH.sub.3                                                                               OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH(CH.sub.2 OH)CH.sub.3                                                                      CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH(CH.sub.2 OSO.sub.2 CH.sub.3)CH.sub.3                                                      CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                H       CH.sub.3                                                                               CH.sub.3 CH                                      CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                          H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                              H       Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                       CH.sub.3                                                                               OCH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                     CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                       CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 SH                                                                         CH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         CH.sub.3                                                                               Cl      OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 SH                                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         H       OCH.sub.3                                                                              OCH.sub.3                                                                               CH                                      CH.sub.2 CH.sub.2 SH                                                                         H       CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                H       CH.sub.3                                                                               OCH.sub.3                                                                               N                                       CH.sub.2 CH.sub.2 SCOCH.sub.3                                                                H       CH.sub.3                                                                               OCH.sub.3                                                                               CH                                      ______________________________________                                    

                                      TABLE 13                                     __________________________________________________________________________      ##STR36##                                                                                                                   m.p.                             R.sub.1        R.sub.5  R.sub.6 X    Y    Z   (°C.)                     __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub. 2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                 H        H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                       CH.sub.3 H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                           H        CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SOCH.sub.3                                                                  CH.sub.3 CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                 H        H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH(OH)CH.sub.2 OH                                                                    H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                        H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                         H        CH.sub.3                                                                               OCH.sub. 3                                                                          OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                        CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                               CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                 CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                              CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub. 3                                                                               CH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________      ##STR37##                                                                                                                   m.p.                             R.sub.1        R.sub.5  R.sub.6 X    Y    Z   (°C.)                     __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                 H        H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                       CH.sub.3 H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                           H        CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SOCH.sub.3                                                                  CH.sub.3 CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                 H        H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH(OH)CH.sub.2 OH                                                                    H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                        H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                         H        CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                        CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                               CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                 CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                              CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________      ##STR38##                                                                                                                   m.p.                             R.sub.1        R.sub.5  R.sub.6 X    Y    Z   (°C.)                     __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                 H        H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                       CH.sub.3 H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                           H        CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SOCH.sub.3                                                                  CH.sub.3 CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                 H        H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH(OH)CH.sub.2 OH                                                                    H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                        H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                         H        CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                        CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                               CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                 CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                              CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   __________________________________________________________________________

                                      TABLE 16                                     __________________________________________________________________________      ##STR39##                                                                                                                   m.p.                             R.sub.1        R.sub.5  R.sub.6 X    Y    Z   (°C.)                     __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          H        CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                 H        H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH(OSO.sub.2 CH.sub.3)CH.sub.3                                                       CH.sub.3 H       Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                           H        CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SOCH.sub.3                                                                  CH.sub.3 CH.sub.3                                                                               Cl   OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OCF.sub.2 H                                                                 H        H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH(OH)CH.sub.2 OH                                                                    H        H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                        H        CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                         H        CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OPO(OCH.sub.3).sub.2                                                        CH.sub.3 H       CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                               CH.sub.3 H       OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.2 CH.sub.3                                                 CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 CH(OH)CH.sub.3                                                              CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.3                                                                       H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CH.sub.2 CH.sub.3                                                              H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.2 CHCH.sub.2                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          C.sub.6 H.sub.5                                                                         H       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.3                                                                      CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                                                             OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               CH.sub.3                                                                            OCH.sub.3                                                                           CH                                   CH.sub.2 CH.sub.2 SH                                                                          CH.sub.3 CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   __________________________________________________________________________

                                      TABLE 17                                     __________________________________________________________________________      ##STR40##                                                                     R.sub.1        R.sub.2 X      Y     Z   m.p. (°C.)                      __________________________________________________________________________     CH.sub.2 CH.sub.2 OH                                                                          3-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-Cl    CH.sub.3                                                                              CH.sub.3                                                                             CH  153-155(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            CH  92-95(d)                               CH.sub.2 CH.sub.2 OH                                                                          5-Cl    OCH.sub.3                                                                             OCH.sub.3                                                                            CH  95-98(d)                               CH.sub.2 CH.sub.2 OH                                                                          5-Cl    Cl     OCH.sub.3                                                                            CH  101-104(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            N   143-146(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-Cl    OCH.sub.3                                                                             OCH.sub.3                                                                            N   108-111(d)                             CH.sub.2 CH.sub.2 OH                                                                          6-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          3-F     CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-F     CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          6-F     CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-Br    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                             CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.3                                                                             Cl     OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CF.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CF.sub.3                                                                             OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                                                                             CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            Cl     OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N    98-101(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-OCF.sub.2 H                                                                          CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-SCF.sub.2 H                                                                          CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub. 2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         5-Cl    Cl     OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                 5-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OCON(CH.sub.3).sub.2                                                        5-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OSO.sub.2 N(CH.sub.3 .sub.2                                                 5-CF.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OCO.sub.2 CH.sub.3                                                          5-OCH.sub.5                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 SOCH.sub.3                                                                  5-SCH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                                                                             CH                                         CH.sub.2 CH.sub.2 OCH.sub.2 CF.sub.3                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OCSNHCH.sub.3                                                               3-F     CH.sub.3                                                                              OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                               6-F     CH.sub.3                                                                              CH.sub.3                                                                             CH                                         CH.sub.2 CH.sub.2 OPO(OC.sub.2 H.sub.3).sub.2                                                 5-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OSi(CH.sub.3).sub.3                                                         5-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                           5-Br    CH.sub.3                                                                              OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                 5-CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                 5-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH(OH)CH.sub.3                                                                       5-CF.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                        5-CF.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-Cl    OCH.sub.2 CH.sub.3                                                                    NHCH.sub.3                                                                           N   134-136(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                                                                             CH   98-102(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            CH  128-131(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                            CH  103-106(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.3                                                                            Cl     OCH.sub.3                                                                            CH  100-103(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                            N   135-137(d)                             CH.sub.2 CH.sub.2 OH                                                                          5-SCH.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                    NHCH.sub.3                                                                           N                                          CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                    NHCH.sub.3                                                                           N                                          CH.sub.2 CH.sub.2 OH                                                                          5-OCH.sub.3                                                                            OCH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                              CH.sub.3                                                                             CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                              OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 OCH.sub.3                                                                   Cl     OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 SCH.sub.3                                                                   CH.sub.3                                                                              CH.sub.3                                                                             CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 SCH.sub.3                                                                   CH.sub.3                                                                              OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 SCH.sub.3                                                                   OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 SCH.sub.3                                                                   Cl     OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 SCH.sub.3                                                                   CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 OH                                                                          5-CH.sub.2 SCH.sub.3                                                                   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 SH                                                                          5-OCH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 SH                                                                          5-OCH.sub.3                                                                            Cl     OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 SH                                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 SH                                                                          5-Cl    OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 SH                                                                          5-Cl    CH.sub.3                                                                              OCH.sub.3                                                                            N                                          CH.sub.2 CH.sub.2 SH                                                                          5-SCH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                         CH.sub.2 CH.sub.2 SH                                                                          5-SCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                            N                                          __________________________________________________________________________

                  TABLE 18                                                         ______________________________________                                          ##STR41##                                                                     R.sub.1      R.sub.2     X.sub.3  m.p. (°C.)                            ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                        H           CH.sub.3                                              CH.sub.2 CH.sub.2 OH                                                                        H           OCH.sub.3                                             CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H           OCH.sub.3                                             CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                        H           CH.sub.3                                              CH.sub.2 CH(OH)CH.sub.3                                                                     H           CH.sub.3                                              CH.sub.2 CH(OH)CH.sub.3                                                                     H           OCH.sub.3                                             CH.sub.2 CH.sub.2 OH                                                                        3-Cl        OCH.sub.3                                             CH.sub.2 CH.sub.2 OH                                                                        5-Cl        OCH.sub.3                                             CH.sub.2 CH.sub.2 OH                                                                        5-CH.sub.3  OCH.sub.3                                             CH.sub.2 CH.sub.2 OH                                                                        5-OCH.sub.3 OCH.sub.3                                             CH.sub.2 CH.sub.2 OH                                                                        5-SCH.sub.3 OCH.sub.3                                             CH.sub.2 CH.sub.2 OH                                                                        5-CH.sub.2 OCH.sub.3                                                                       OCH.sub.3                                             CH.sub.2 CH.sub.2 OH                                                                        6-Cl        OCH.sub.3                                             CH.sub.2 CH.sub.2 SH                                                                        H           CH.sub.3                                              CH.sub.2 CH.sub.2 SH                                                                        H           OCH.sub.3                                             ______________________________________                                    

                  TABLE 19                                                         ______________________________________                                          ##STR42##                                                                                                            m.p.                                    R.sub.1     R.sub.2    X.sub.4   Y.sub.4                                                                              Z(°C.)                           ______________________________________                                         CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3  CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3  CH.sub.3                                                                             N                                       CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3  OCH.sub.3                                                                            CH                                      CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3  OCH.sub.3                                                                            N                                       CH.sub.2 CH.sub.2 OH                                                                       H          OCH.sub.3 CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OH                                                                       H          OCH.sub.3 CH.sub.3                                                                             N                                       CH.sub.2 CH.sub.2 OH                                                                       H          Cl        CH.sub.3                                                                             N                                       CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.3  Cl    CH                                      CH.sub.2 CH.sub.2 OH                                                                       H          CH.sub.2 OCH.sub.3                                                                       CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub. 3                                                      H          CH.sub.3  CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                       H          CH.sub.3  CH.sub.3                                                                             N                                       CH.sub.2 CH.sub.2 OH                                                                       5-Cl       CH.sub.3  CH.sub.3                                                                             N                                       CH.sub.2 CH.sub.2 OH                                                                       5-Cl       CH.sub.3  CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OH                                                                       5-OCH.sub.3                                                                               CH.sub.3  CH.sub.3                                                                             N                                       CH.sub.2 CH.sub.2 OH                                                                       5-OCH.sub.3                                                                               CH.sub.3  CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OH                                                                       5-SCH.sub.3                                                                               CH.sub.3  CH.sub.3                                                                             N                                       CH.sub.2 CH.sub.2 OH                                                                       5-SCH.sub.3                                                                               CH.sub.3  CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OH                                                                       5-CF.sub.3 CH.sub.3  CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OH                                                                       5-CH.sub.3 CH.sub.3  CH.sub.3                                                                             CH                                      CH.sub.2 CH.sub.2 OH                                                                       5-CH.sub.2 OCH.sub.3                                                                      CH.sub.3  CH.sub.3                                                                             CH                                      ______________________________________                                    

                  TABLE 20                                                         ______________________________________                                          ##STR43##                                                                     R.sub.2   X          Y         Z     m.p. (°C.)                         ______________________________________                                         H         CH.sub.3   CH.sub.3  CH                                              H         CH.sub.3   OCH.sub.3 CH                                              H         OCH.sub.3  OCH.sub.3 CH                                              H         Cl         OCH.sub.3 CH    130(d)                                    H         CH.sub.3   CH.sub.3  N                                               H         CH.sub.3   OCH.sub.3 N                                               H         OCH.sub.3  OCH.sub.3 N                                               H         OCH.sub.3  N(CH.sub.3).sub.2                                                                        N                                               H         OCH.sub.2 CH.sub.3                                                                        NHCH.sub.3                                                                               N                                               5-Cl      OCH.sub.3  OCH.sub.3 CH                                              5-OCH.sub.3                                                                              OCH.sub.3  OCH.sub.3 CH                                              5-SCH.sub.3                                                                              OCH.sub.3  OCH.sub.3 CH                                              5-CH.sub.2 OCH.sub.3                                                                     OCH.sub.3  OCH.sub.3 CH                                              3-Cl      OCH.sub.3  OCH.sub.3 CH                                              6-Cl      OCH.sub.3  OCH.sub.3 CH                                              5-CH.sub.3                                                                               OCH.sub.3  OCH.sub.3 CH                                              5-CF.sub.3                                                                               OCH.sub.3  OCH.sub.3 CH                                              ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE 21                                                         ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 6 Wettable Powder

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 80%

sodium alkylnaphthalenesulfonate: 2%

sodium ligninsulfonate: 2%

synthetic amorphous silica: 3%

kaolinite: 13%

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 7 Wettable Powder

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 50%

sodium alkylnaphthalenesulfonate: 2%

low viscosity methyl cellulose: 2%

diatomaceous earth: 46%

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 8 Granule

Wettable Powder of Example 7: 5%

attapulgite granules (U.S.S. 20-40 mesh; 0.84-0.42 mm): 95%

A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules while tumbling in a double-cone blender. The granules are dried and packaged.

EXAMPLE 9 Extruded Pellet

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 25%

anhydrous sodium sulfate: 10%

crude calcium ligninsulfonate: 5%

sodium alkylnaphthalenesulfonate: 1%

calcium/magnesium bentonite: 59%

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 10 Oil Suspension

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 25%

polyoxyethylene sorbitol hexaoleate: 5%

highly aliphatic hydrocarbon oil: 70%

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 11 Wettable Powder

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 20%

sodium alkylnaphthalenesulfonate: 4%

sodium ligninsulfonate: 4%

low viscosity methyl cellulose: 3%

attapulgite: 69%

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 12 Low Strength Granule

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 1%

N,N-dimethylformamide: 9%

attapulgite granules (U.S.S. 20-40 sieve): 90%

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 13 Aqueous Suspension

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 40%

polyacrylic acid thickener: 0.3%

dodecylphenol polyethylene glycol ether: 0.5%

disodium phosphate: 1%

monosodium phosphate: 0.5%

polyvinyl alcohol: 1.0%

water: 56.7%

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 14 Solution

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester, sodium salt: 5%

water: 95%

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 15 Low Strength Granule

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 0.1%

attapulgite granules (U.S.S. 20-40 mesh): 99.9%

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 16 Granule `-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 80%

wetting agent: 1%

crude ligninsulfonate salt (containing 5-20% of the natural sugars): 10%

attapulgite clay: 9%

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 17 High Strength Concentrate

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 99%

silica aerogel: 0.5%

synthetic amorphous silica: 0.5%

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 18 Wettable Powder

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 90%

dioctyl sodium sulfosuccinate: 0.1%

synthetic fine silica: 9.9%

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 19 Wettable Powder

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 40%

sodium ligninsulfonate: 20%

montmorillonite clay: 40%

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 20 Oil Suspension

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 35%

blend of polyalcohol carboxylic esters and oil soluble petroleum sulfonates: 6%

xylene: 59%

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 21 Dust

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester: 10%

attapulgite: 10%

Pyrophyllite: 80%

The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Utility

Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat. Alternatively, the subject compounds are useful to modify plant growth.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide; examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

    ______________________________________                                         Compounds                                                                       ##STR44##                                                                     Com-                                                                           pound                                                                          No.   R.sub.1          R.sub.2                                                                              X     Y      Z                                    ______________________________________                                          1    CH.sub.2 CH.sub.2 OH                                                                            H     CH.sub.3                                                                             CH.sub.3                                                                              CH                                    2    CH.sub.2 CH.sub.2 OH                                                                            H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                    3    CH.sub.2 CH.sub.2 OH                                                                            H     Cl    OCH.sub.3                                                                             CH                                    4    CH.sub.2 CH.sub.2 OH                                                                            H     CH.sub.3                                                                             OCH.sub.3                                                                             N                                     5    CH.sub.2 CH.sub.2 OH                                                                            H     OCH.sub.3                                                                            OCH.sub.3                                                                             N                                     6    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            H     CH.sub.3                                                                             CH.sub.3                                                                              CH                                    7    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                    8    CH.sub.2 CH.sub. 2 OSO.sub.2 CH.sub.3                                                           H     Cl    OCH.sub.3                                                                             CH                                    9    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            H     CH.sub.3                                                                             OCH.sub.3                                                                             N                                    10    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            H     OCH.sub.3                                                                            OCH.sub.3                                                                             N                                    11    CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   H     CH.sub.3                                                                             CH.sub.3                                                                              CH                                   12    CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   H     CH.sub.3                                                                             OCH.sub.3                                                                             CH                                   13    CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                   14    CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   H     Cl    OCH.sub.3                                                                             CH                                   15    CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   H     CH.sub.3                                                                             CH.sub.3                                                                              N                                    16    CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   H     CH.sub.3                                                                             OCH.sub.3                                                                             N                                    17    CH.sub.2 CH.sub.2 CH.sub.2 OH                                                                   H     OCH.sub.3                                                                            OCH.sub.3                                                                             N                                    18    (CH.sub.2).sub.3 OSO.sub.2 CH.sub.3                                                             H     CH.sub.3                                                                             CH.sub.3                                                                              CH                                   19    (CH.sub.2).sub.3 OSO.sub.2 CH.sub.3                                                             H     CH.sub.3                                                                             OCH.sub.3                                                                             CH                                   20    (CH.sub.2).sub.3 OSO.sub.2 CH.sub.3                                                             H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                   21    (CH.sub.2).sub.3 OSO.sub.2 CH.sub.3                                                             H     Cl    OCH.sub.3                                                                             CH                                   22    (CH.sub.2 ).sub.3 OSO.sub.2 CH.sub.3                                                            H     CH.sub.3                                                                             CH.sub.3                                                                              N                                    23    (CH.sub.2).sub.3 OSO.sub.2 CH.sub.3                                                             H     CH.sub.3                                                                             OCH.sub.3                                                                             N                                    24    (CH.sub.2).sub.3 OSO.sub.2 CH.sub.3                                                             H     OCH.sub.3                                                                            OCH.sub.3                                                                             N                                    25    CH.sub.2 CH.sub.2 OH                                                                            H     CH.sub.3                                                                             CH.sub.3                                                                              N                                    26    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            H     CH.sub.3                                                                             CH.sub.3                                                                              N                                    27    CH.sub.2 CH.sub.2 OC(O)CH.sub.3                                                                 H     CH.sub.3                                                                             CH.sub.3                                                                              CH                                   28    CH.sub.2 CH.sub.2 OC(O)CH.sub.3                                                                 H     CH.sub.3                                                                             OCH.sub.3                                                                             CH                                   29    CH.sub.2 CH.sub.2 OC(O)CH.sub.3                                                                 H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                   30    CH.sub.2 CH.sub.2 OC(O)CH.sub.3                                                                 H     CH.sub.3                                                                             OCH.sub.3                                                                             N                                    31    CH.sub.2 CH.sub.2 OC(O)CH.sub.3                                                                 H     OCH.sub.3                                                                            OCH.sub.3                                                                             N                                    32    CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 H     CH.sub.3                                                                             OCH.sub.3                                                                             CH                                   33    CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                   34    CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 H     Cl    OCH.sub.3                                                                             CH                                   35    CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 H     CH.sub.3                                                                             OCH.sub.3                                                                             N                                    36    CH.sub.2 CH.sub.2 OSO.sub.2 -n-C.sub.8 H.sub.17                                                 H     OCH.sub.3                                                                            OCH.sub.3                                                                             N                                    37    CH(CH.sub.3)CH.sub.2 OSO.sub.2 CH.sub.3                                                         H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                   38    CH.sub.2 CH.sub.2 OC(O)NHA*                                                                     H     Cl    OCH.sub.3                                                                             CH                                   39    CH.sub.2 CH(OH)CH.sub.3                                                                         H     CH.sub.3                                                                             CH.sub.3                                                                              CH                                   40    CH.sub.2 CH(OH)CH.sub.3                                                                         H     CH.sub.3                                                                             OCH.sub.3                                                                             CH                                   41    CH.sub.2 CH(OH)CH.sub.3                                                                         H     OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                   42    CH.sub.2 CH(OH)CH.sub.3                                                                         H     Cl    OCH.sub.3                                                                             CH                                   43    CH.sub.2 CH(OH)CH.sub.3                                                                         H     CH.sub.3                                                                             OCH.sub.3                                                                             N                                    44    CH.sub.2 CH(OH)CH.sub.3                                                                         H     OCH.sub.3                                                                            OCH.sub.3                                                                             N                                    45    CH.sub.2 CH.sub.2 OH                                                                            Cl    CH.sub.3                                                                             CH.sub.3                                                                              CH                                   46    CH.sub.2 CH.sub.2 OH                                                                            Cl    CH.sub.3                                                                             OCH.sub.3                                                                             CH                                   47    CH.sub.2 CH.sub.2 OH                                                                            Cl    OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                   48    CH.sub.2 CH.sub.2 OH                                                                            Cl    Cl    OCH.sub.3                                                                             CH                                   49    CH.sub.2 CH.sub.2 OH                                                                            Cl    CH.sub.3                                                                             OCH.sub.3                                                                             N                                    50    CH.sub.2 CH.sub.2 OH                                                                            Cl    OCH.sub.3                                                                            OCH.sub.3                                                                             N                                    51    CH.sub.2 CH.sub.2 OH                                                                            Cl    OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                                                            N                                    52    CH.sub.2 CH.sub.2 OH                                                                            H     OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                                                            N                                    53    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                            H     OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                                                            N                                    ______________________________________                                          *A is 4chloro-6-methoxypyrimidin-2-yl                                    

Test A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea spp.), cocklebur (Xanthium Pensylvanicum), sorghum, corn, soybean, cotton, sugar beet, rice, wheat and purple nutsedge (Cyperus routundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to &=complete kill. The accompanying descriptive symbols have the following meanings:

B=burn;

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation;

X=axillary stimulation;

S=albiniusm; and

6Y=abscised buds or flowers.

    TABLE A       TYPE RATE MORNING COCKLE- VELVET- NUT- CRAB BARNYARD CHEAT WILD SICKLE       SOY-  SOR-   TEST K/HA GLORY BUR LEAF SEDGE GRASS GRASS GRASS OATS POD      WHEAT CORN BEAN RICE GHUM SUGARBEET COTTON        Compound 1 POST 0.05 9C 9C 7C 2C 9C 2C 9C 2C 3U 3C 7C 3U 3C 2C POST      0.05   9G 5G  8G  8G 9G 9G 9G 9G 9H 9G PRE 0.05 9G 9H 8E 3C 4C 2C 9G 7C      9G 9H 8E 8E 5C 4C PRE 0.05    7G 9H 9G  9H     9G 9G Compound 2 POST      0.05 8C 9C 9C 3C 9C 3C 9C 8C 7U 6C 9C 9C 9C 8C POST 0.05    8G  9G   9C      9G PRE 0.05 9G 9H 8E 7G 5C 4C 4C 5C 9G 9H 8E 8H 5C 8C PRE 0.05     9H 9G      9H 9H     9G Compound 3 POST 0.05 4C 9C 3C 8G 9C 1C 3C 5G 2C 2C 5C 3C 9C 5      C POST 0.05 9G  9G   2G 3H  7H 7H 9G 9G  9G PRE 0.05 9G 9H 8E 2C 4C 3C      5C 3C 2U 4C 8E 8H 5C 9G PRE 0.05     9H 8G 9G 9G 9G 8G   9G Compound 4      POST 0.05 2C 3C 2C 1H 3C 0 0 2G 3U 5C 4G 3U 3C 4C POST 0.05 4H 5G 6G  9H         9G 9G  9G 6G 7H PRE 0.05 3C 8H 3G 2G 3C 2C 3C 0 2C 2C 3C 3C 6G 7G PRE      0.05 7G    3H  8G  9G 3H 6G 9H Compound 5 POST 0.05 2C 2C 3G 0 3C 0 1C 0 2      U 3C 2G 3C 3C 2C POST 0.05 3G    9H    9H 9G  8G 4H 5G PRE 0.05 3G 0 0 0      1C 0 0 0 8G 3H 2C 2C 5G 5G PRE 0.05            8H Compound 6 POST 0.05      6C 6C 9G 3C 9C 4C 4C 3C 2U 4C 9C 5C 9C 5C POST 0.05 9G 9G  6G  9G 8H 9G      9H 9G  9G  9G PRE 0.05 9G 8H 9G 5G 5C 3C 7G 3C 3C 3C 8E 5C 8E 9G PRE      0.05     9H 9G  9H 9G 7H  9H Compound 7 POST 0.05 9C 9C 8C 3C 9C 9C 9C      4C 3U 9C 9C 3U 9C 9C POST 0.05    7G    9G 9G   9G PRE 0.05 9H 9H 8E 7G      9H 9G 5C 5C 9G 9H 8E 8H 9C 9G PRE 0.05       9G 9H Compound 8 POST 0.05      8C 9C 3C 4H 9H 6C 4C 7C 4H 2C 5C 4C 3C 9C POST 0.05   9G   9G 6G 9G  8G      9G 9G 7G PRE 0.05 9G 8H 8E 5G 4C 2C 3C 2C 2C 3C 8E 8H 4C 2C PRE 0.05      9H 6G 6G 8G 8G 7G   9G 9G Compound 9 POST 0.05 2C 9C 0 2G 2C 7G 4C 6G 2C 2      C 2G 3C 5C 4C POST 0.05 4H    7H  8H  9H 7G  9H 9G 8H PRE 0.05 7G 7H 0 0      0 0 3C 0 8G 3H 2C 2C 5C 7G PRE 0.05       6G     9G 9G Compound 10 POST      0.05 3C 4C 3G 0 3H 0 4C 0 3H 2C 3G 3H 5C 4C POST 0.05 6G 9G     8H   4G       9G 8G PRE 0.05 8G 8H 0 0 0 0 7G 0 3C 2C 0 2C 5C 3C PRE 0.05         6G       6G 9G 7G Compound 11 POST 0.05 2C 4C 2C 2G 9H 1C 2C 8G 3C 4H 4C 3C 3C      2C POST 0.05 5H 9H 5G      7H  9G 7H 7H 6G PRE 0.05 2G 6H 0 0 1H 0 2G 0      3G 2G 3G 4G 4H 5G Compound 12 POST 0.05 3C 4C 3C 3G 9H 1C 3C 3G 3C 5C 5C 2      C 3C 9C POST 0.05 7H 9G 8G    5G  7H 9G 9G 7H 7H PRE 0.05 8G 8H 5G 0 3C      5G 3C 5G 2C 9H 3C 2C 8G 9G PRE 0.05     9H  7H  8G  8H 8G Compound 13      POST 0.05 3G 5C 3C 3G 9C 0 3C 0 2C 4C 3C 3C 5G 9C POST 0.05  9G 8G    7G       5H 8H 9G 8H PRE 0.05 5G 8H 0 0 3C 0 7G 3G 6G 8H 5G 7G 6G 9G PRE 0.05       9H Compound 14 POST 0.05 2G 4C 0 0 9H 0 1C 0 0 2H 2C 1C 0 5C POST 0.05      9H         6G 5G  9G PRE 0.05 5G 8H 0 0 3C 0 3C 0 4G 0 0 3G 4G 6G PRE      0.05     6G  4G Compound 15 POST 0.05 0 4C 0 0 2C 0 0 0 2G 0 2G 0 0 0      POST 0.05  9H   4H PRE 0.05 0 5G 0 0 0 0 0 0 0 0 0 0 0 0 Compound 16      POST 0.05 1C 3C 0 0 3C 0 4G 0 4C 3H 3G 8G 4C 7G POST 0.05 4G 9H   5H      9H    9H PRE 0.05 0 5H 0 0 0 0 0 0 2G 0 2C 0 2C 0 PRE 0.05      5H Compound 17 POST 0.05 2G 2C 0 2G 3C 0 2C 0 4G 3H 0 3G 4C 0 POST 0.05      8H   5H  3G      8H PRE 0.05 7G 4G 0 0 0 0 3H 0 0 0 0 0 5H 0 Compound 18 P      OST 0.05 3C 5C 3C 2G 3C 2C 3C 3C 8G 1C 7H 5C 4C 4C 4C POST 0.05 8H 9G 8G       8H  8G 3G  2H  9G 9G 8H 9H PRE 0.05 2H 3H 3G 0 1H 0 2C 1C 0 2C 2C 2C 3C      8E 8G PRE 0.05       4G   3G  4G 9H Compound 19 POST 0.05 9C 8C 9G 3C 3C 3      C 3C 4C 5G 2C 9H 5C 4C 9C 9C POST 0.05    5G 9H 8G 9G 8H  3H  9G 9G PRE      0.05 9G  2C 3C 4C 5C 3C 4C 6G 2C 3C 5C 6C 4C 8G PRE 0.05   8G 7G 9H 9G      7G 7G  7G 6H 9H 9H 9G Compound 20 POST 0.05 3C 8C 5C 2G 3C 3C 3G 3C 3G      2G 3C 5C 3C 4C 9C POST 0.05 8G  9G  9H 7G  7H   9G 9G 9H 8H PRE 0.05 7G      7H 5G 3G 5H 7G 5G 5G 0 6G 6H 2C 3C 9G 8G PRE 0.05            6G 9H      Compound 21 POST 0.05 3C 9C 3C 0 3C 0 3G 3C 2G 1C 3G 3C 5C 3C 5C POST      0.05 5H  6G  7H   3H  3H  8G 9H 7H 9G PRE 0.05 5G 5H 4G 3G 2G 0 0 2G 0      4G 0 4G 2C 8G 6G PRE 0.05             9H Compound 22 POST 0.05 0 0 0 0 0 0       0 0 0 0 0 0 0 0 0 PRE 0.05 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compound 23      POST 0.05 3C 4C 0  0 0 3C 0 3C 0 2G 2C 0 3C 4C 4C POST 0.05 7G 9G    5G         6H  9H 9H 8H PRE 0.05 2C 2C 0 0 0 0 0 0 0 2C 0 0 3C 3C 0 PRE 0.05  5H             5G   9H 3H Compound 24 POST 0.05 3C 3C 0 0 0 0 0 2C 0 0 2C 0 3C      3C 6G POST 0.05 5H 9H         5H  6H 8H PRE 0.05 0 2C 0 0 0 0 0 0 0 0 0      0 0 0 0 PRE 0.05  2H Compound 25 POST 0.05 8C 8C 5C 1C 9C 5C 0 9C 0 3H      5C 5C 9H 9C 9C POST 0.05   9G 4G  8G     9G 9G PRE 0.05 9G  8E 0 5C 4C      3C 3C 2G 2C 6H 5C 4C 9G 9G PRE 0.05     9H 9G 7G 7H  8H  9G 9H Compound      26 POST 0.05 9C 8C 4C 5G 5C 3C 3C 2C 3G 3C 5C 5C 2C 9C 9C POST 0.05   9G       9H 9G 6G 8H  9H 9H 9G 9G PRE 0.05 9G 9H 8E 1C 3C 4C 3C 8G 6G 9G 3C 8E      5C 9G 9G PRE 0.05     9H 9G 9H    8H  9H Compound 27 POST 0.05 6C 5C 5C      3C 9C 2C 6C 9G 3C 6C 9C 5C 5C 9C POST 0.05 9G 9G 9G 8G  8G 9G  9H 9G  9H      9G PRE 0.05 9G 9H 3C 2C 4C 3C 3C 4C 5C 4C 8E 5C 5C 9G PRE 0.05   9G 4G      9H 7G 9G 8H 9H 8H  9H 9G  Compound 28 POST 0.05 8C 8C 6C 3C 9C 2C 9C 2C      3C 9C 9C 5C 9C 9C POST 0.05   9G 6G  8G  9G 9G   9G PRE 0.05 9G 9G 8E 3C      5C 3C 4C 3C 9H 9H 8E 5C 6C 3C PRE 0.05    7G 9H 9G 9G 9G    9H 9G 9G      Compound 29 POST 0.05 8C 8C 9C 3C 8C 2C 8C 9G 2C 4C 9C 3C 9C 9C POST      0.05    9G  9G   9G 9G  9G PRE 0.05 9G 9H 8E 7G 5C 2C 8G 5C 9H 9H 8E 6C      9C 5C PRE 0.05     9H 8H  9H    9H  9G Compound 30 POST 0.05 2C 2C 0 2G      3C 0 3G 0 4C 4C 2C 3C 3C 3C POST 0.05 4H 4G   8H    9H 8H 5G 9H 4G 9H      PRE 0.05 2C 2C 0 0 2G 0 0 0 2C 2C 5G 3C 5G 5G PRE 0.05         9G 3H  9G C      ompound 31 POST 0.05 3C 3G 0 0 2C 0 0 0 2C 2C 2C 3C 4C 3C POST 0.05 5G       8H    6H 5H 4G 8G 5H 6G PRE 0.05 3C 8G 0 0 2C 0 4G 0 2C 5H 2C 2C 2C 5G      PRE 0.05 5G        8G   5G 5G Compound 32 POST 0.05 8C 9C 9C 4C 3C 9C 8C 3      C 2C 6C 9C 9C 9C 8C 5C POST 0.05    8G 3G   8G 9G 9G     9G PRE 0.05 5C      9H 5C 8E 2C 4C 8E 3C 3C 4C 4C 8E 5C 5C 9G PRE 0.05 9H  9G  3G 9H  9G 9G      9G 8G  9H 9G Compound 33 POST 0.05 8C 8C 8C 9C 3C 9C 8C 2C 2C 8C 8C 9C      8C 8C 9C POST 0.05     6G   9G 8G PRE 0.05 9G 9H 5C 8E 2C 3C 9H 3C 2C 2C      2C 8E 3C 9C 9G PRE 0.05   9G  5G 9H  8G 8G 9G 8G  9H Compound 34 POST      0.05 8C 4C 3C 4C 0 5C 4C 2C 2C 2C 5C 4C 9C 9C 4C POST 0.05  9G 7G 9G  9H      8G 3G 4G 6H 9H 9G   9G PRE 0.05 8G 8H 8G 8G 0 3C 7G 3G 2C 7G 2C 9G 3C 5C      8G PRE 0.05      7G   5G  6G  9H 9G Compound 35 POST 0.05 4C 8C 9C  0 0      0 4G 0 0 3C 2C 0 3C 8C 4C POST 0.05 8G         8H 8G  9H  9H PRE 0.05 7G      6H 6G 0 0 0 2G 0 0 3C 4H 2C 3C 5C 8G PRE 0.05          8H   9H 9G      Compound 36 POST 0.05 3C 8C 4C 2C 0 0 0 0 0 2H 4H 0 0 3C 3C POST 0.05 8G       8G           9H 7G PRE 0.05 8G 2C 0 0 0 0 0 0 0 2C 1C 0 3G 9C 6G PRE      0.05  5G        4G Compound 37 POST 0.05 3C 8C 9C 4C 3G 9C 8G 4C 5C 3C      4C 9C 3C 9C 5C POST 0.05 7G   9G    8G 9G 9H 9G  9H  9G PRE 0.05 8G 9H      5C 8E 0 5C 5C 4C 4C 3C3C5C5C 8C9G PRE0.059G 9H9G9G 9H8H9H 9H Compound 38 P      OST 0.05 3C 9C 5C 4C 0 3C 2C 0 0 3C 4C 4C 4C 4C 5C POST 0.05 7H  9G 9G      9H 4G   7G 8G 8G 9H 8H 9G PRE 0.05 9G 8H 7G 8G 2G 3C 0 0 4G 3C 3C 4C 7C      4C 3C PRE 0.05      8H    7G 6H 9H 9H 8G 8G Compound 39 POST 0.05 3C 8C      2C 2C 2C 5C 2C 0 0 2U 5C 6C 4C 8C 4C POST 0.05 8G  9G 9G  9H 9G   9G 9G      9G 9G  8H PRE 0.05 7G 9H 3C 6G 0 7H 7G 2C 3G 3C 2C 9H 9H 5C 2C PRE 0.05       5H     5G  8H 6G   9G 6H Compound 40 POST 0.05 9C 9C 9C 2C 3G 9C 8G 2C      8G 3U 5C 6C 6C 9C 8C POST 0.05    9G    5G  9G 9G 9G 9G PRE 0.05 9G 9H      2C 8E 2G 4C 9H 3C 2C 2C 9H 8E 9H 5C 3C PRE 0.05   8G   9H  8H 9H 9H      9G 9G Compound 41 POST 0.05 8C 8C 8C 8C 5G 9C 3C 2C 7G 8C 9C 5C 4C 8C 8C      POST 0.05       9G 6G    9G 9G PRE 0.05 9G  9G 8E 0 5C 9H 4C 2C 2C 9H 8E      8H 4C 9G PRE 0.05      9H  8G 9H 9H    9G Compound 42 POST 0.05 2C 9C 2C 8      G 0 9H 3G 0 0 1H 2C 5C 5C 4C 9C POST 0.05 9H  8G       5G 9G 9G 9G 9H      PRE 0.05 7G 8H 5G 8E 0 8H 0 2G 5G 4G 2C 9H 9H 3C 8G PRE 0.05      2H   8G Compound 43 POST 0.05 2C 3C 2C 2C 0 3C 1C 0 0 9C 4C 4G 3C 3C 2C      POST 0.05 6H 8H 6G 8G       8H  9G 8H 3G PRE 0.05 3H 2H 0 0 0 0 0 0 0 2C      5H 0 3C 8G 0 PRE 0.05          5G   8H Compound 44 POST 0.05 2C 2C 2G 7G 0       2H 0 0 0 8H 3H 0 2C 2C 0 POST 0.05 5H 5G         7G  6G 6H PRE 0.05 0      4H 3G 0 0 0 0 0 0 5G 2G 0 2C 0 0 PRE 0.05             5G Compound 45      POST 0.05 2C 9C 9C 2C 4G 9C 3C 0 2C 9C 9C 2C 3C 3H 9C POST 0.05 6H   8G        8G  5G   5G 9H PRE 0.05 8G 9H 8H 5G 2G 8H 8G 2G 7G 9G 7H 2C 3C 7G 8G      PRE 0.05            8G 9H Compound 46 POST 0.05 6C 8C 8C 3C 5G 9C 7G 0      5G 9C 9C 5C 4C 3C 8C POST 0.05 9G   8G        9G 9H 5H PRE 0.05 9G 9H 4C      3C 3G 5C 8G 8G 3C 3C 8H 8E 3C 4C 2C PRE 0.05   9G 9G  9H   9G 9H   9H 9G      8G Compound 47 POST 0.05 5C 9C 8C 4C 3G 9C 6G 0 3G 5C 9C 4C 3C 2C 9C      POST 0.05 9G   9G      9G  9G 9H 6G PRE 0.05 9G 9H 8C 4C 2C 3C 6G 2G 8G      3C 9H 4C 2C 8G 4C PRE 0.05    9G 3G 9H    9H  9H 9H  9G Compound 48 POST 0      .05 5C 9C 4C 2C 0 4C 0 0 0 0 5C 2C 4C 1C 2C POST 0.05 9G  8G 7G  9H      9G 8G 9H  5G PRE 0.05 5G 8G 8G 0 0 3G 2G 1C 4G 7G 2H 7H 3C 5G 6G PRE      0.05             7G Compound 49 POST 0.05 4G  4C 2G 0 0 6C 5G 2G 5G 5C      3C 3C 3C 2C 0 POST 0.05  9H    9H    9G 7G 7G 8H 3G PRE 0.05 4H 0 0 0 0      3C 5G 2C 5G 3C 3H 3C 2C 0 0 PRE 0.05      6G  8G  9G  6H 7G Compound 50      POST 0.05 0 4H 0 0 0 4C 4G 0 0 3C 3C 4C 1C 3C 0 POST 0.05      9H    9H      6H 9G  5H PRE 0.05 0 2H 4H 0 0 0 4G 2C 5G 3C 2G 3C 3C 6G 2G PRE 0.05         6G  8G  8H 8G Compound 51 POST 0.05 2C 8G 3C 5G 2G 5C 3G 0 0 3C 3C 5C 3      C 2C 2C POST 0.05 8G  7G   9H    9H 9H 9G 7H 2H PRE 0.05 6G 7G 7G 0 4G      2C 8G 2C 8G 8G 5H 3C 3C 3G 2G PRE 0.05      8G  8G    8H 7G Compound 52      POST 0.05 3C 4C 4C 2C 3G 5C 3C 6G 2G 5C 9C 9C 5C 9C 5C POST 0.05 8H 9G      9G 5G  9H 8G   9G   9G  9G PRE 0.05 9C 8G 9G 5G 6G 9H 9H 9G 8G 9G 9H 9H      9H 5C 9G PRE 0.05              9G Compound 53 POST 0.05 4C 3C 4C 0 3G 5C 4      C 9G 0 3U 5C 9C 4C 9C 4C POST 0.05 8H 6G 8H   9H 9G   9G 9G  9H  9G PRE      0.05 9G 8H 3C 5G 3G 9H 9H 3C 2G 9G 3C 4C 3C 5C 2C PRE 0.05   7G     8G      7H 9H 9H 9G 9G 

What is claimed is:
 1. A compound of the formula : ##STR45## wherein J is ##STR46## W is O or S; R is H or CH₃ ;R₁ is C₂ -C₅ alkyl, C₄ akenyl or C₄ alkynyl substituted with one or two substituents selected from: ##STR47## provided that (1) when R₁ is disubstituted, then the two substituents are identical and are not on the same carbon atom; and (2) the carbon atom of R₁ adjacent to the ester oxygen does not carry any of the above substituents and must be substituted by at least one hydrogen atom; W₁ is O or S; R₂ is H, Cl, F, Br, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkoxy, C₁ -C₃ haloalkylthio, C₁ -C₂ haloalkyl, or C₁ -C₂ alkyl substituted with OCH₃ or SCH₃ ; R₃ is H, F, Cl, CH₃ or OCH₃ ; R₄ is H or CH₃ ; R₅ is H, C₁ -C₃ alkyl, CH₂ CH═CH₂ or phenyl; R₆ is H or C₁ -C₃ alkyl; R₈ is H or C₁ -C₂ alkyl; R₉ is C₁ -C₂ alkyl; R₁₀ is C₁ -C₄ alkyl or C₆ H₅ ; A is ##STR48## X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, OCF₂ H, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃ or CF₃ ; Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, NH₂, N(CH₃)₂, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, ##STR49## OCF₂ H, SCF₂ H, CH₂ S(O)_(p) (C₁ -C₄ alkyl), cyclopropyl or CH₂ OC₂ H₅ ; m is 2 or 3; p is 0, 1 or 2; Q₁ and Q₂ are independently O or S; R₁₃ is H or CH₃ ; R₁₄ and R₁₅ are independently C₁ -C₂ alkyl; R₁₆ is H, F, Cl or CH₃ ; R₁₇ is C₁ -C₁₀ alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 methoxy groups or 0-1 cyano groups, C₃ -C₁₀ alkenyl substituted with 0-3 atoms of F, Cl or Br, C₃ -C₁₀ alkynyl substituted with 0-3 atoms of F, Cl or Br, or ##STR50## Z is CH; X₄ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl; and Y₄ is CH₃, OCH₃, OC₂ H₅ or Cl;provided that (a) when W is S, then R is H. A is ##STR51## and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CF₃, OCH₂ CH₂ OCH₃, CH(OCH₃)₂ or ##STR52## (b) when X is Cl, F or Br, then Y is OCH₃, OC₂ H₅, NH₂, N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂ H;and their agriculturally suitable salts.
 2. A compound of claim 1 wherein W is O; R is H; R₁ is monosubstituted C₂ -C₅ alkyl; R₇ is CH₃, C₂ H₅, C₃ alkenyl or C₃ alkynyl; R₉ is CH₃ ; R₁₀ is CH₃ ; and R₁₇ is C₁ -C₄ alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 methoxy groups or 0-1 cyano group, C₃ -C₄ alkenyl substituted with 0-3 atoms of F, Cl or Br or C₃ -C₄ alkynyl.
 3. A compound of claim 2 wherein A is A-1; R₂ is H, F, Cl, CH₃, OCH₃, OC₂ H₅, SCH₃, SC₂ H₅, CH₂ OCH₃ or CF₃ ; R₆ is H; R₁₆ is H; and Y is CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, CH₂ OC₂ H₅, NHCH₃, N(CH₃)₂, cyclopropyl, CH(OCH₃)₂ or ##STR53##
 4. A compound of claim 3 wherein R₁₇ is CH₃, C₂ H₅ or CH₂ CH═CH₂ ; W₁ is O; and R₁ is monosubstituted C₂ -C₃ alkyl.
 5. A compound of claim 4 wherein J is J-1 and R₂ is H.
 6. A compound of claim 4 wherein J is J-2.
 7. A compound of claim 4 wherein J is J-3.
 8. A compound of claim 4 wherein J is J-4.
 9. A compound of claim 4 wherein J is J-5.
 10. A compound of claim 4 wherein J is J-6.
 11. A compound of claim 4 wherein J is J-7.
 12. A compound of claim 4 wherein J is J-8.
 13. A compound of claim 4 wherein X is CH₃, OCH₃, OC₂ H₅, Cl, Br, OCHF₂ or CF₃ ; and Y is CH₃, OCH₃, NHCH₃ or CH(OCH₃)₂.
 14. A compound of claim 1 which is 2-[[(4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoic acid, 2-hydroxyethyl ester.
 15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 16. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 17. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 18. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 19. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 20. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
 21. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 22. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
 23. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 25. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 26. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 27. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 5. 28. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 6. 29. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 7. 30. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 8. 